N-(1,3,4-oxadiazol-2-yl)arylcarboxamides and use thereof as herbicides

ABSTRACT

N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides of the general formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I) A is nitrogen or CY. R, X, Y and Z are each radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.

The invention relates to the technical field of herbicides, especiallythat of herbicides for selective control of broad-leaved weeds and weedgrasses in crops of useful plants.

Under CAS No. 876870-49-4, 1024115-81-8, 920483-67-6, 1208906-74-4,1178717-16-2 and 1178627-20-7, the compounds2,4-difluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide,2,4-dimethyl-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide,2,4-dimethoxy-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide,N-(5-benzyl-1,3,4-oxadiazol-2-yl)-2-chloro-4-fluorobenzamid,2-bromo-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-4-fluorobenzamide and4-bromo-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-2-fluorobenzamide areknown. Faming Zhuanli Shenqing Gongkai Shuomingshu (1996), 17 pp.,discloses the compound2,4-dichloro-N-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzamide. WO2010/132404 A1 discloses the compounds2-hydroxy-4-methoxy-N-[5-(pentafluoroethyl)-1,3,4-oxadiazol-2-yl]benzamideand2-acetoxy-4-methyl-N-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]benzamide.US 2009163545 A1 discloses N-(1,3,4-oxadiazol-2-yl)nicotinamides havingpharmacological properties. Indian Journal of Chemistry, Section B:Organic Chemistry Including Medicinal Chemistry (1986), 25B(12), 1266-8discloses 2-halo-N-(1,3,4-oxadiazol-2-yl)nicotinamides and6-halo-N-(1,3,4-oxadiazol-2-yl)nicotinamides. No herbicidal action ofthese compounds has been disclosed to date. EP 0 049 071 describes theherbicidal action ofN-[5-(1-ethyl-1-methylpropyl)-1,3,4-oxadiazol-2-yl]-2,6-dimethoxybenzamide.WO 2011/035674 A1 discloses N-(1,2,5-oxadiazol-3-yl)benzamides and usethereof as herbicides.

It has now been found that N-(1,3,4-oxadiazol-2-yl)arylcarboxamides areof particularly good suitability as herbicides. The present inventionprovides N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of the formula (I) orsalts thereof

in which the substituents are defined as follows:

A is N or CY,

R is hydrogen, (C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, CH₂R⁶,(C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR¹, NHR¹,methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl,dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl,methylsulfonyl, or heteroaryl, heterocyclyl, benzyl or phenyl eachsubstituted by s radicals from the group of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

X is nitro, halogen, cyano, formyl, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OR¹, OCOR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², NR₁, R₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,(C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, where the two latterradicals are each substituted by s halogen, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy radicals, and where heterocyclyl bears n oxo groups,

Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,CO(NOR¹)R¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-COOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylphenyl,(C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, phenyl, heteroarylor heterocyclyl, where the 6 latter radicals are each substituted by sradicals from the group of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl andcyanomethyl, and where heterocyclyl bears n oxo groups,

Z is halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)_(n)R²,SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, heteroaryl, heterocyclyl or phenyl, where the threelatter radicals are each substituted by s radicals from the group ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy orhalo-(C₁-C₆)-alkoxy, and where heterocyclyl bears n oxo groups, or Z mayalso be hydrogen if Y is the S(O)_(n)R² radical,

R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,

R⁵ is methyl or ethyl,

R⁶ is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido,N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,dimethylaminocarbonyl, (C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, orheteroaryl, heterocyclyl or phenyl each substituted by s radicals fromthe group of methyl, ethyl, methoxy, trifluoromethyl and halogen,

n is 0, 1 or 2;

s is 0, 1, 2 or 3,

with the proviso that

-   a) X and Z are not both the same radical from the group of chlorine,    fluorine, methoxy and methyl when Y is hydrogen,-   b) X is not hydroxyl when Y is hydrogen and Z is methoxy,-   c) X is not chlorine or bromine when Y is hydrogen and Z is    fluorine,-   d) X is not fluorine when Y is hydrogen and Z is bromine,-   e) X or Z is not hydrogen when A is nitrogen,-   f) R is not trifluoromethyl when X is acetoxy and Z is methyl.

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-,iso-, tert- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and1,3,-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, semisaturated or fully unsaturated cyclicradical containing 3 to 6 ring atoms, of which 1 to 4 are from the groupof oxygen, nitrogen and sulfur, and which may additionally be fused by abenzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl,tetrahydrofuranyl, dihydrofuranyl and oxetanyl,

Heteroaryl is an aromatic cyclic radical containing 3 to 6 ring atoms,of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, andwhich may additionally be fused by a benzo ring. For example, heteroarylis benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl,oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl,benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

When a group is polysubstituted by radicals, this means that this groupis substituted by one or more identical or different radicals from thosementioned.

According to the nature and the bonding of the substituents, thecompounds of the general formula (I) may be present as stereoisomers.When, for example, one or more asymmetric carbon atoms are present,enantiomers and diastereomers may occur. Stereoisomers likewise occurwhen n is 1 (sulfoxides). Stereoisomers can be obtained from themixtures obtained in the preparation by customary separation methods,for example by chromatographic separation processes. It is equallypossible to selectively prepare stereoisomers by using stereoselectivereactions using optically active starting materials and/or auxiliaries.The invention also relates to all stereoisomers and mixtures thereofwhich are encompassed by the general formula (I) but not definedspecifically.

Particular preference is given to compounds of the general formula (I)in which

A is N or CY,

R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazin-2-yl,furan-2-yl, tetrahydrofuran-2-yl, morpholine, dimethylamino, or phenylsubstituted by s radicals from the group of methyl, methoxy,trifluoromethyl and halogen;

X is nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, where the two latter radicals are eachsubstituted by s halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy radicals,and where heterocyclyl bears n oxo groups,

Y hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,(C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl,phenyl, heteroaryl or heterocyclyl, where the 6 latter radicals are eachsubstituted by s radicals from the group of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylbears n oxo groups,

Z is halogen, cyano, nitro, methyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)R², 1,2,4-triazol-1-yl, pyrazol-1-yl, or

Z may also be hydrogen if Y is the S(O)_(n)R² radical,

R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe 16 latter radicals are substituted by s radicals from the groupconsisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³,COR^(S), OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where these three aforementionedradicals are each substituted by s radicals from the group consisting ofhalogen and OR³,

R³ is hydrogen or (C₁-C₆)-alkyl,

R⁴ is (C₁-C₆)-alkyl,

n is 0, 1 or 2;

s is 0, 1, 2 or 3,

with the proviso that

-   a) X and Z are not both the same radical from the group of chlorine,    fluorine, methoxy and methyl when Y is hydrogen,-   b) X is not hydroxyl when Y is hydrogen and Z is methoxy,-   c) X is not chlorine or bromine when Y is hydrogen and Z is    fluorine,-   d) X is not fluorine when Y is hydrogen and Z is bromine,-   e) X or Z is not hydrogen when A is nitrogen,-   f) R is not trifluoromethyl when X is acetoxy and Z is methyl.

In all the formulae specified hereinafter, the substituents and symbolshave the same definition as in formula (I), unless defined differently.

Inventive compounds can be prepared, for example, by the method shown inscheme 1, by base-catalyzed reaction of a benzoyl or nicotinyl chloride(II) with a 2-amino-1,3,4-oxadiazole (III):

The benzoyl chlorides of the formula (II) or the parent benzoic acidsthereof are known in principle and can be prepared, for example, by themethods described in U.S. Pat. No. 6,376,429 B1, EP 1 585 742 A1 and EP1 202 978 A1.

Inventive compounds can also be prepared by the method described inscheme 2, by reacting a benzoic or nicotinic acid of the formula (IV)with a 2-amino-1,3,4-oxadiazole (III):

For the activation, it is possible to use dehydrating reagents which aretypically used for amidation reactions, for example1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC),2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P)etc.

Inventive compounds can also be prepared by the method described inscheme 3, by cyclizing a compound of the formula V:

The cyclization can be performed by the methods described in Synth.Commun. 31 (12), 1907-1912 (2001) or in Indian J. Chem., Section B:Organic Chemistry Including Medicinal Chemistry; Vol. 43 (10), 2170-2174(2004).

The compound of the formula V used in scheme 3 can be prepared byreaction of an acyl isocyanate of the formula VII with a hydrazide ofthe formula VI by the method described in Synth. Commun. 25(12),1885-1892 (1995).

It may be appropriate to alter the sequence of reaction steps. Forinstance, benzoic acids bearing a sulfoxide cannot be converted directlyto their acid chlorides. One option here is first to prepare the amideto the thioether stage and then to oxidize the thioether to thesulfoxide.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the abovementioned reactions can also be preparedin a parallelized manner, in which case this may be accomplished in amanual, partly automated or fully automated manner. It is possible here,for example, to automate the conduct of the reaction, the workup or thepurification of the products and/or intermediates. Overall, this isunderstood to mean a procedure as described, for example, by D. Tiebesin Combinatorial Chemistry—Synthesis, Analysis, Screening (editor:Günther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MultiPROBE Automated Workstationsfrom Perkin Elmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the formula (I) and salts thereof or ofintermediates which occur in the course of preparation, availableapparatuses include chromatography apparatuses, for example from ISCO,Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be purchased, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, the compounds of the generalformula (I) and salts thereof can be prepared completely or partially bysolid-phase supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis,Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use ofsolid phase-supported synthesis methods permits a number of protocolsknown from the literature, and these may again be executed manually orin an automated manner. The reactions can be performed, for example, bymeans of IRORI technology in microreactors from Nexus Biosystems, 12140Community Road, Poway, Calif. 92064, USA.

Either on a solid phase or in the liquid phase, the performance ofsingle or multiple synthesis steps can be supported by the use ofmicrowave technology. The technical literature describes a number ofexperimental protocols, for example Microwaves in Organic and MedicinalChemistry (editors: C. O. Kappe and a. Stadler), Wiley, 2005.

The preparation by the processes described here gives compounds of theformula (I) and salts thereof in the form of substance collections,which are called libraries. The present invention also provideslibraries comprising at least two compounds of the formula (I) and saltsthereof.

The inventive compounds of the formula (I) (and/or salts thereof),collectively referred to hereinafter as “inventive compounds”, haveexcellent herbicidal efficacy against a broad spectrum of economicallyimportant monocotyledonous and dicotyledonous annual harmful plants. Theactive ingredients also have good control over perennial weed plantswhich are difficult to control and produce shoots from rhizomes, rootstocks or other perennial organs.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more inventive compound(s) is/are appliedto the plants (for example weed plants such as monocotyledonous ordicotyledonous weeds or unwanted crop plants), to the seeds (for examplegrains, seeds or vegetative propagules such as tubers or shoot partswith buds) or to the area on which the plants grow (for example the areaunder cultivation). The inventive compounds can be deployed, forexample, prior to sowing (if appropriate also by incorporation into thesoil), prior to emergence or after emergence. Specific examples of somerepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the inventive compounds are as follows,though the enumeration is not intended to impose a restriction toparticular species:

Monocotyledonous Harmful Plants of the Genera:

Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria,Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium,Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa,Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa,Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous Weeds of the Genera:

Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia,Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia,Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo,Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca,Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio,Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria,Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the inventive compounds are applied to the soil surface beforegermination, either the weed seedlings are prevented completely fromemerging or the weeds grow until they have reached the cotyledon stage,but then stop growing and, eventually, after three to four weeks havepassed, die completely.

If the active ingredients are applied post-emergence to the green partsof the plants, there is likewise stoppage of growth after the treatment,and the harmful plants remain at the growth stage of the time ofapplication, or they die completely after a certain time, such thatcompetition by the weeds, which is harmful to the crop plants, is thuseliminated very early and in a lasting manner.

Although the inventive compounds have excellent herbicidal activityagainst monocotyledonous and dicotyledonous weeds, crop plants ofeconomically important crops, for example dicotyledonous crops of thegenera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus,Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana,Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of thegenera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum,Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea andTriticum, are damaged only to an insignificant extent, if at all,depending on the structure of the respective inventive compound and theapplication rate thereof. For these reasons, the present compounds arevery suitable for selective control of unwanted plant growth in plantcrops such as agriculturally useful plants or ornamentals.

In addition, the inventive compounds (depending on their particularstructure and the application rate deployed) have outstandinggrowth-regulating properties in crop plants. They intervene in theplant's own metabolism with a regulatory effect, and can thus be used tocontrol plant constituents and to facilitate harvesting, for example bytriggering desiccation and stunted growth. In addition, they are alsosuitable for general control and inhibition of unwanted vegetativegrowth without killing the plants. Inhibiting vegetative growth plays amajor role for many monocotyledonous and dicotyledonous crops, since,for example, this can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth-regulating properties,the active ingredients can also be used for control of harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, transgenic plants are notable for specialadvantageous properties, for example for resistances to certainpesticides, in particular certain herbicides, resistances to plantdiseases or organisms that cause plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or with a different fatty acidcomposition in the harvested material.

With regard to transgenic crops, preference is given to the use of theinventive compounds in economically important transgenic crops of usefulplants and ornamentals, for example of cereals such as wheat, barley,rye, oats, millet/sorghum, rice and corn, or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. Preferably, the inventive compounds can be used asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

Preference is given to the use of the inventive compounds or saltsthereof in economically important transgenic crops of useful plants andornamentals, for example of cereals such as wheat, barley, rye, oats,millet/sorghum, rice, cassava and corn, or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. Preferably, the inventive compounds can be used asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to plants which have occurred to date consist,for example, in traditional breeding methods and the generation ofmutants. Alternatively, novel plants with modified properties can begenerated with the aid of recombinant methods (see, for example,EP-A-0221044, EP-A-0131624). For example, there have been manydescriptions of:

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type    -   (WO 92/00377) or of the sulfonylurea type (EP-A-0257993, U.S.        Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, with the ability to        produce Bacillus thuringiensis toxins (Bt toxins) which make the        plants resistant to particular pests (EP-A-0142924,        EP-A-0193259).    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        cause an increased disease resistance (EPA 309862, EPA0464461),    -   genetically modified plants with reduced photorespiration, which        have higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are notable for higher yields or        better quality,    -   transgenic crop plants which are notable for a combination, for        example, of the abovementioned novel properties (“gene        stacking”).

Numerous molecular biology techniques which can be used to produce noveltransgenic plants with modified properties are known in principle; see,for example, I. Potrykus and G. Spangenberg (eds.), Gene Transfer toPlants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelbergor Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or a sequence change by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. For the connection ofthe DNA fragments to one another, it is possible to add adapters orlinkers to the fragments; see, for example, Sambrook et al., 1989,Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring HarborLaboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene andKlone”, VCH Weinheim, 2nd edition, 1996.

The production of plant cells with a reduced activity of a gene productcan be achieved, for example, by the expression of at least oneappropriate antisense RNA, or of a sense RNA for achievement of acosuppression effect, or the expression of at least one appropriatelyconstructed ribozyme which specifically cleaves transcripts of theabovementioned gene product. For this purpose, it is firstly possible touse DNA molecules which comprise the entire coding sequence of a geneproduct including any flanking sequences present, or else DNA moleculeswhich comprise only parts of the coding sequence, in which case theseparts must be long enough to bring about an antisense effect in thecells. It is also possible to use DNA sequences which have a high degreeof homology to the coding sequences of a gene product, but are notcompletely identical.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, in order to achieve localization in a particularcompartment, it is possible, for example, to join the coding region toDNA sequences which ensure localization in a particular compartment.Such sequences are known to those skilled in the art (see, for example,Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl.Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991),95-106). The nucleic acid molecules can also be expressed in theorganelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive whole plants. In principle, the transgenic plants may be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

Thus, it is possible to obtain transgenic plants whose properties arealtered by overexpression, suppression or inhibition of homologous(=natural) genes or gene sequences, or expression of heterologous(=foreign) genes or gene sequences.

Preferably, the inventive compounds can be used in transgenic cropswhich are resistant to growth regulators, for example dicamba, or toherbicides which inhibit essential plant enzymes, for exampleacetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS)or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from thegroup of the sulfonylureas, the glyphosates, glufosinates orbenzoylisoxazoles and analogous active ingredients.

On employment of the inventive active ingredients in transgenic crops,not only do the effects toward harmful plants observed in other cropsoccur, but often also effects which are specific to application in theparticular transgenic crop, for example an altered or specificallywidened spectrum of weeds which can be controlled, altered applicationrates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also provides for the use of the inventivecompounds as herbicides for control of harmful plants in transgenic cropplants.

The inventive compounds can be applied in the form of wettable powders,emulsifiable concentrates, sprayable solutions, dusting products orgranules in the customary formulations. The invention therefore alsoprovides herbicidal and plant growth-regulating compositions whichcomprise the inventive compounds.

The inventive compounds can be formulated in various ways, according tothe biological and/or physicochemical parameters required. Examples ofpossible formulations include: wettable powders (WP), water-solublepowders (SP), water-soluble concentrates, emulsifiable concentrates(EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions,sprayable solutions, suspension concentrates (SC), oil- or water-baseddispersions, oil-miscible solutions, capsule suspensions (CS), dustingproducts (DP), seed-dressing products, granules for broadcasting andsoil application, granules (GR) in the form of microgranules, sprayablegranules, coated granules and adsorption granules, water-dispersiblegranules (WG), water-soluble granules (SG), ULV formulations,microcapsules and waxes. These individual types of formulation are knownin principle and are described, for example, in: Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], volume 7, C. HanserVerlag Munich, 4th edition 1986, Wade van Valkenburg, “PesticideFormulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying”Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley &Sons, N.Y., C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y.1963, McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler,“Chemische Technologie”, Band 7, C. Hanser Verlag Munich, 4th ed. 1986.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and with safeners,fertilizers and/or growth regulators, for example in the form of afinished formulation or as a tankmix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active ingredient, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonateor else sodium oleoylmethyltaurate. To produce the wettable powders, theactive herbicidal ingredients are ground finely, for example incustomary apparatus such as hammer mills, blower mills and air-jetmills, and simultaneously or subsequently mixed with the formulationassistants.

Emulsifiable concentrates are produced by dissolving the activeingredient in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). The emulsifiersused may, for example, be: calcium alkylarylsulfonates such as calciumdodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acidpolyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycolethers, propylene oxide-ethylene oxide condensation products, alkylpolyethers, sorbitan esters, for example sorbitan fatty acid esters, orpolyoxyethylene sorbitan esters, for example polyoxyethylene sorbitanfatty acid esters.

Dusting products are obtained by grinding the active ingredient withfinely distributed solid substances, for example talc, natural clays,such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of commercial bead millswith optional addition of surfactants as already listed above, forexample, for the other formulation types. Emulsions, for exampleoil-in-water emulsions (EW), can be produced, for example, by means ofstirrers, colloid mills and/or static mixers using aqueous organicsolvents and optionally surfactants as already listed above, forexample, for the other formulation types. Granules can be producedeither by spraying the active ingredient onto adsorptive granulatedinert material or by applying active ingredient concentrates by means ofadhesives, for example polyvinyl alcohol, sodium polyacrylate or mineraloils, to the surface of carrier substances, such as sand, kaolinites orgranulated inert material. Suitable active ingredients can also begranulated in the manner customary for the production of fertilizergranules—if desired as a mixture with fertilizers. Water-dispersiblegranules are produced generally by the customary processes such asspray-drying, fluidized bed granulation, pan granulation, mixing withhigh-speed mixers and extrusion without solid inert material. For theproduction of pan granules, fluidized bed granules, extruder granulesand spray granules, see, for example, processes in “Spray-DryingHandbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning,“Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry'sChemical Engineers Handbook”, 5th ed., McGraw-Hill, New York 1973, p.8-57. For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of inventive compounds.

In wettable powders, the active ingredient concentration is, forexample, about 10 to 90% by weight; the remainder to 100% by weightconsists of the customary formulation constituents. In emulsifiableconcentrates, the active ingredient concentration may be about 1 to 90%and preferably 5 to 80% by weight. Dust-type formulations contain 1 to30% by weight of active ingredient, preferably usually 5 to 20% byweight of active ingredient; sprayable solutions contain about 0.05 to80% and preferably 2 to 50% by weight of active ingredient. In the caseof water-dispersible granules, the active ingredient content dependspartly on whether the active compound is present in liquid or solid formand on which granulation assistants, fillers, etc., are used. In thewater-dispersible granules, the content of active ingredient is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active ingredient formulations mentioned optionallycomprise the respective customary tackifiers, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and with safeners,fertilizers and/or growth regulators, for example in the form of afinished formulation or as a tankmix.

Usable combination partners for the inventive compounds in mixtureformulations or in a tankmix are, for example, known active ingredientsbased on inhibition of, for example, acetolactate synthase, acetyl-CoAcarboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphatesynthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase,phytoendesaturase, photosystem I, photosystem II, protoporphyrinogenoxidase, as described, for example, in Weed Research 26 (1986) 441-445or “The Pesticide Manual”, 15th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 2009 and literature citedtherein. Examples of known herbicides or plant growth regulators whichcan be combined with the inventive compounds include the activeingredients which follow (the compounds are designated by the commonname according to the International Organization for Standardization(ISO) or by the chemical name or by the code number) and alwaysencompass all use forms, such as acids, salts, esters and isomers, suchas stereoisomers and optical isomers. In this list, one or else, in somecases, more than one application form is mentioned:

acetochlor, acibenzolar, acibenzolar-5-methyl, acifluorfen,acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim,alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron,aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate,ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron,aziprotryne, beflubutamid, benazolin, benazolin-ethyl, bencarbazone,benfluralin, benfuresate, bensulide, bensulfuron, bensulfuron-methyl,bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor,benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium,bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim,bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil,butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole,carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen,chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam,chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol,chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl,chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl,chlortoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin,cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet,clomazone, clomeprop, cloprop, clopyralid, cloransulam,cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide,cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop,cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB,daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham,desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil,dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron,difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium,dimefuron, dikegulac-sodium, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine,dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide,dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb,ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon,ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl,ethoxysulfuron, etobenzanid, F-5331, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide,F-7967, i.e.3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin,flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn,fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,flupoxam, flupropacil, flupropanate, flupyrsulfuron,flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol,flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen,foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid,glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,glyphosate-isopropylammonium, H-9201, i.e.O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate,halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl,imazamox, imazamox-ammonium, imazapic, imazapyr,imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr,imazethapyr-ammonium, imazosulfuron, inabenfide, indanofan, indaziflam,indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron,iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isocarbamid,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, KUH-043, i.e.3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide,MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium,mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium,mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide,mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione,methabenzthiazuron, metam, metamifop, metamitron, metazachlor,metazasulfuron, methazole, methiopyrsulfuron, methiozolin,methoxyphenone, methyldymron, 1-methylcyclopropene, methylisothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor,metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl,molinate, monalide, monocarbamide, monocarbamide dihydrogensulfate,monolinuron, monosulfuron, monosulfuron ester, monuron, MT-128, i.e.6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine,MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide,NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium(isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquatdichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin,penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen,pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor,primisulfuron, primisulfuron-methyl, probenazole, profluazole,procyazine, prodiamine, prifluraline, profoxydim, prohexadione,prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide,prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil,pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate),pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz,pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb,pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl,pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone,pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop,quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim,siduron, simazine, simetryn, SN-106279, i.e. methyl(2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate,sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron,sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron,SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e.1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl,thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone,triallate, triasulfuron, triaziflam, triazofenamide, tribenuron,tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane,trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin,triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac,trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P,vernolate, ZJ-0862, i.e.3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, andthe following compounds:

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Dust-type formulations, granulesfor soil application or granules for broadcasting and sprayablesolutions are not normally diluted further with other inert substancesprior to application.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including temperature, humidity and thetype of herbicide used. It can vary within wide limits, for examplebetween 0.001 and 1.0 kg/ha or more active substance, but it ispreferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES 1. Preparation ofN-(5-benzyl-1,3,4-oxadiazol-2-yl)-2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzamide(Ex. No. 6-198)

90 mg (0.26 mmol) of2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoicacid and 45 mg (0.26 mmol) of 5-benzyl-1,3,4-oxadiazol-2-amine aredissolved at room temperature (RT) in 8 ml of CH₂Cl₂. Then 248 mg (0.398mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide(50% solution in THF) are added, the mixture is stirred at RT for onehour and then 0.181 ml (1.3 mmol) of triethylamine, 6 mg (0.052 mmol) of4-dimethylaminopyridine are added. Then the mixture is stirred at RT for20 h and washed twice with 4 ml each time of water, dried over Na₂SO₄and concentrated. The residue is purified by column chromatography(prep. HPLC; acetonitrile/water). Yield 70 mg (45%).

¹H NMR (400 MHz; DMSO-d₆): 12.49 ppm (s broad 1H); 8.08 (d, 1H), 7.92(d, 1H), 7.39-7.24 (m, 5H), 5.23 (s, 2H), 4.27 (q, 2H), 3.39 (s, 3H).

2. Preparation of2-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)nicotinamide(Ex. No. 7-3)

200 mg (0.887 mmol) of 2-chloro-6-(trifluoromethyl)nicotinic acid and100 mg (0.887 mmol) of 5-ethyl-1,3,4-oxadiazol-2-amine are dissolved atRT in 8 ml of CH₂Cl₂. Then 846 mg (1.33 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) are added, the mixture is stirred at RT for one hourand then 0.618 ml (4.43 mmol) of triethylamine, 22 mg (0.177 mmol) of4-dimethylaminopyridine are added. The reaction mixture is stirred at RTfor 20 h and then washed twice with 4 ml each time of water, dried oversodium sulfate and concentrated. The residue is purified by columnchromatography (prep. HPLC; acetonitrile/water). Yield 80 mg (28%).

¹H NMR (400 MHz; DMSO-d₆): 12.59 ppm (s broad 1H); 8.49 (d, 1H), 8.11(d, 1H), 2.85 (q, 2H), 1.28 (t, 3H).

3. Preparation of2-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-4-(methylsulfonyl)benzamide(Ex. No. 3-9)

415 mg (1.77 mmol) of 2-chloro-4-(methylsulfonyl)benzenecarboxylic acidand 200 mg (1.77 mmol) of 5-ethyl-1,3,4-oxadiazol-2-amine are dissolvedat RT in 9 ml of CH₂Cl₂. Then 1.68 g (2.64 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) are added, the mixture is stirred at RT for one hourand then 0.246 ml (1.77 mmol) of triethylamine, 43 mg (0.35 mmol) of4-dimethylaminopyridine are added. The reaction mixture is stirred at RTfor 48 h and then washed twice with 4 ml each time of water, andpurified by column chromatography (prep. HPLC; acetonitrile/water).Yield 41 mg (6%).

¹H NMR (400 MHz; DMSO-d₆): 12.55 ppm (s broad 1H); 8.12 (s, 1H), 8.01(d, 1H), 7.92 (d, 1H), 3.35 (s, 3H), 2.84 (q, 2H), 1.26 (t, 3H).

The abbreviations used mean:

-   -   Et=ethyl Me=methyl n-Pr=n-propyl i-Pr=isopropyl c-Pr=cyclopropyl        Ph=phenyl Ac=acetyl Bz=benzoyl

TABLE 1 Inventive compounds of the general formula (I) in which A is CYand R is hydrogen

Physical data No. X Y Z (¹H NMR, DMSO-d₆, 400 MHz) 1-1 F H Cl 1-2 F HSO₂Me 1-3 F H SO₂Et 1-4 F H CF₃ 1-5 F H NO₂ 1-6 Cl H Br 1-7 Cl H SMe 1-8Cl H SOMe 1-9 Cl H SO₂Me 1-10 Cl H SO₂CH₂Cl 1-11 Cl H SEt 1-12 Cl HSO₂Et 1-13 Cl H CF₃ 1-14 Cl H NO₂ 1-15 Cl H pyrazol-1-yl 1-16 Cl H1H-1,2,4- triazol-1-yl 1-17 Br H Cl 1-18 Br H Br 1-19 Br H SO₂Me 1-20 BrH SO₂Et 1-21 Br H CF₃ 1-22 SO₂Me H Cl 1-23 SO₂Me H Br 1-24 SO₂Me H SMe1-25 SO₂Me H SOMe 1-26 SO₂Me H SO₂Me 1-27 SO₂Me H SO₂Et 1-28 SO₂Me H CF₃1-29 SO₂Et H Cl 1-30 SO₂Et H Br 1-31 SO₂Et H SMe 1-32 SO₂Et H SOMe 1-33SO₂Et H SO₂Me 1-34 SO₂Et H CF₃ 1-35 NO₂ H F 1-36 NO₂ H Cl 1-37 NO₂ H Br1-38 NO₂ H I 1-39 NO₂ H CN 1-40 NO₂ H SO₂Me 1-41 NO₂ H SO₂Et 1-42 NO₂ HCF₃ 1-43 Me H Cl 1-44 Me H Br 1-45 Me H SMe 1-46 Me H SO₂Me 1-47 Me HSO₂CH₂Cl 1-48 Me H SEt 1-49 Me H SO₂Et 1-50 Me H CF₃ 1-51 CH₂SO₂Me H CF₃1-52 Et H Cl 1-53 Et H Br 1-54 Et H SMe 1-55 Et H SO₂Me 1-56 Et HSO₂CH₂Cl 1-57 Et H SEt 1-58 Et H SO₂Et 1-59 Et H CF₃ 1-60 CF₃ H Cl 1-61CF₃ H Br 1-62 CF₃ H SO₂Me 1-63 CF₃ H SO₂Et 1-64 CF₃ H CF₃ 1-65 NO₂ NH₂ F1-66 NO₂ NHMe F 1-67 NO₂ NMe₂ F 1-68 NO₂ Me Cl 1-69 NO₂ NH₂ Cl 1-70 NO₂NHMe Cl 1-71 NO₂ NMe₂ Cl 1-72 NO₂ NH₂ Br 1-73 NO₂ NHMe Br 1-74 NO₂ NMe₂Br 1-75 NO₂ NH₂ CF₃ 1-76 NO₂ NMe₂ CF₃ 1-77 NO₂ NH₂ SO₂Me 1-78 NO₂ NH₂SO₂Et 1-79 NO₂ NHMe SO₂Me 1-80 NO₂ NMe₂ SO₂Me 1-81 NO₂ NMe₂ SO₂Et 1-82NO₂ NH₂ 1H-1,2,4- triazol-1-yl 1-83 NO₂ NHMe 1H-1,2,4- triazol-1-yl 1-84NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 1-85 Me SMe H 1-86 Me SOMe H 1-87 MeSO₂Me H 1-88 Me SEt H 1-89 Me SOEt H 1-90 Me SO₂Et H 1-91 Me S(CH₂)₂OMeH 1-92 Me SO(CH₂)₂OMe H 1-93 Me SO₂(CH₂)₂OMe H 1-94 Me F F 1-95 Me F Cl1-96 Me SEt F 1-97 Me SOEt F 1-98 Me SO₂Et F 1-99 Me Me Cl 1-100 Me F Cl1-101 Me Cl Cl 1-102 Me NH₂ Cl 1-103 Me NHMe Cl 1-104 Me NMe₂ Cl 1-105Me O(CH₂)₂OMe Cl 1-106 Me O(CH₂)₃OMe Cl 1-107 Me O(CH₂)₄OMe Cl 1-108 MeOCH₂CONMe₂ Cl 1-109 Me O(CH₂)₂—CO—NMe₂ Cl 1-110 Me O(CH₂)₂— ClNH(CO)NMe₂ 1-111 Me O(CH₂)₂— Cl NH(CO)NHCO₂Et 1-112 Me O(CH₂)₂—NHCO₂MeCl 1-113 Me OCH₂—NHSO₂cPr Cl 1-114 Me O(CH₂)-5-2,4- Cl dimethyl-2,4-dihydro-3H-1,2,4- triazol-3-one 1-115 Me O(CH₂)-3,5- Cldimethyl-1,2-oxazol- 4-yl 1-116 Me SMe Cl 1-117 Me SOMe Cl 1-118 MeSO₂Me Cl 1-119 Me SEt Cl 1-120 Me SOEt Cl 1-121 Me SO₂Et Cl 1-122 MeS(CH₂)₂OMe Cl 1-123 Me SO(CH₂)₂OMe Cl 1-124 Me SO₂(CH₂)₂OMe Cl 1-125 MeNH₂ Br 1-126 Me NHMe Br 1-127 Me NMe₂ Br 1-128 Me OCH₂(CO)NMe₂ Br 1-129Me O(CH₂)-5-pyrrolidin- Br 2-one 1-130 Me SMe Br 1-131 Me SOMe Br 1-132Me SO₂Me Br 1-133 Me SEt Br 1-134 Me SOEt Br 1-135 Me SO₂Et Br 1-136 MeSMe I 1-137 Me SOMe I 1-138 Me SO₂Me I 1-139 Me SEt I 1-140 Me SOEt I1-141 Me SO₂Et I 1-142 Me Cl CF₃ 1-143 Me SMe CF₃ 1-144 Me SOMe CF₃1-145 Me SO₂Me CF₃ 8.03 (d, 1H), 7.97 (d, 1H), 7.54 (s, 1 H), 3.46 (s,3H), 3.42 (s, 3H) 1-146 Me SEt CF₃ 1-147 Me SOEt CF₃ 1-148 Me SO₂Et CF₃1-149 Me S(CH₂)₂OMe CF₃ 1-150 Me SO(CH₂)₂OMe CF₃ 1-151 Me SO₂(CH₂)₂OMeCF₃ 1-152 Me Me SO₂Me 1-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-154Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-155 Me 5-cyanomethyl-4,5- SO₂Medihydro-1,2-oxazol- 3-yl 1-156 Me 5-cyanomethyl-4,5- SO₂Etdihydro-1,2-oxazol- 3-yl 1-157 Me NH₂ SO₂Me 1-158 Me NHMe SO₂Me 1-159 MeNMe₂ SO₂Me 1-160 Me NH(CH₂)₂OMe SO₂Me 1-161 Me pyrazol-1-yl SO₂Me 1-162Me OH SO₂Me 1-163 Me OMe SO₂Me 1-164 Me OMe SO₂Et 1-165 Me OEt SO₂Me1-166 Me OEt SO₂Et 1-167 Me OiPr SO₂Me 1-168 Me OiPr SO₂Et 1-169 MeO(CH₂)₂OMe SO₂Me 1-170 Me O(CH₂)₂OMe SO₂Et 1-171 Me O(CH₂)₃OMe SO₂Me1-172 Me O(CH₂)₃OMe SO₂Et 1-173 Me O(CH₂)₄OMe SO₂Me 1-174 Me O(CH₂)₄OMeSO₂Et 1-175 Me O(CH₂)₂NHSO₂Me SO₂Me 1-176 Me O(CH₂)₂NHSO₂Me SO₂Et 1-177Me OCH₂(CO)NMe₂ SO₂Me 1-178 Me OCH₂(CO)NMe₂ SO₂Et 1-179 Me[1,4]dioxan-2-yl- SO₂Me methoxy 1-180 Me [1,4]dioxan-2-yl- SO₂Et methoxy1-181 Me O(CH₂)₂—O—(3,5-di- SO₂Me methoxypyrimidin-2- yl) 1-182 Me ClSO₂Me 1-183 Me SMe SO₂Me 1-184 Me SOMe SO₂Me 1-185 Me SO₂Me SO₂Me 1-186Me SO₂Me SO₂Et 1-187 Me SEt SO₂Me 1-188 Me SOEt SO₂Me 1-189 Me SO₂EtSO₂Me 1-190 Me S(CH₂)₂OMe SO₂Me 1-191 Me SO(CH₂)₂OMe SO₂Me 1-192 MeSO₂(CH₂)₂OMe SO₂Me 1-193 CH₂SMe OMe SO₂Me 1-194 CH₂OMe OMe SO₂Me 1-195CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 1-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me1-197 CH₂O(CH₂)₃OMe OMe SO₂Me 1-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me1-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 1-200 Et SMe Cl 1-201 Et SO₂Me Cl1-202 Et SMe CF₃ 1-203 Et SO₂Me CF₃ 1-204 Et F SO₂Me 1-205 EtNH(CH₂)₂OMe SO₂Me 1-206 iPr SO₂Me CF₃ 1-207 cPr SO₂Me CF₃ 1-208 CF₃O(CH₂)₂OMe F 1-209 CF₃ O(CH₂)₃OMe F 1-210 CF₃ OCH₂CONMe₂ F 1-211 CF₃[1,4]dioxan-2-yl- F methoxy 1-212 CF₃ O(CH₂)₂OMe Cl 1-213 CF₃ O(CH₂)₃OMeCl 1-214 CF₃ OCH₂CONMe₂ Cl 1-215 CF₃ [1,4]dioxan-2-yl- Cl methoxy 1-216CF₃ O(CH₂)₂OMe Br 1-217 CF₃ O(CH₂)₃OMe Br 1-218 CF₃ OCH₂CONMe₂ Br 1-219CF₃ [1,4]dioxan-2-yl- Br methoxy 1-220 CF₃ O(CH₂)₂OMe I 1-221 CF₃O(CH₂)₃OMe I 1-222 CF₃ OCH₂CONMe₂ I 1-223 CF₃ [1,4]dioxan-2-yl- Imethoxy 1-224 CF₃ F SO₂Me 1-225 CF₃ F SO₂Et 1-226 CF₃ O(CH₂)₂OMe SO₂Me1-227 CF₃ O(CH₂)₂OMe SO₂Et 1-228 CF₃ O(CH₂)₃OMe SO₂Me 1-229 CF₃O(CH₂)₃OMe SO₂Et 1-230 CF₃ OCH₂CONMe₂ SO₂Me 1-231 CF₃ OCH₂CONMe₂ SO₂Et1-232 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 1-233 CF₃ [1,4]dioxan-2-yl-SO₂Et methoxy 1-234 F SMe CF₃ 1-235 F SOMe CF₃ 1-236 Cl Me Cl 1-237 ClOCH₂CHCH₂ Cl 1-238 Cl OCH₂CHF₂ Cl 1-239 Cl O(CH₂)₂OMe Cl 1-240 ClOCH₂CONMe₂ Cl 1-241 Cl O(CH₂)-5-pyrrolidin- Cl 2-one 1-242 Cl SMe Cl1-243 Cl SOMe Cl 1-244 Cl SO₂Me Cl 1-245 Cl F SMe 1-246 Cl Cl SO₂Me1-247 Cl COOMe SO₂Me 1-248 Cl CONMe₂ SO₂Me 1-249 Cl CONMe(OMe) SO₂Me1-250 Cl CH₂OMe SO₂Me 1-251 Cl CH₂OMe SO₂Et 1-252 Cl CH₂OEt SO₂Me 1-253Cl CH₂OEt SO₂Et 1-254 Cl CH₂OCH₂CHF₂ SO₂Me 1-255 Cl CH₂OCH₂CF₃ SO₂Me11.98 (bs, 1H), 8.04 (d, 1H), 7.90 (d, 1H), 5.23 (s, 2H), 4.33- 4.22 (m,2H), 3.36 (s, 3H) 1-256 Cl CH₂OCH₂CF₃ SO₂Et 1-257 Cl CH₂OCH₂CF₂CHF₂SO₂Me 1-258 Cl CH₂OcPentyl SO₂Me 1-259 Cl CH₂PO(OMe)₂ SO₂Me 1-260 Cl4,5-dihydro-1,2- SMe oxazol-3-yl 1-261 Cl 4,5-dihydro-1,2- SO₂Meoxazol-3-yl 1-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-263 Cl5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 1-264 Cl5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 1-265 Cl5-(methoxymethyl)- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 1-266 Cl5-(methoxymethyl)- SO₂Et 5-methyl-4,5- dihydro-1,2-oxazol- 3-yl 1-267 ClCH₂O- SO₂Me tetrahydrofuran-3-yl 1-268 Cl CH₂O- SO₂Ettetrahydrofuran-3-yl 1-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 1-270Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 1-271 Cl CH₂OCH₂- SO₂Metetrahydrofuran-3-yl 1-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 1-273Cl OMe SO₂Me 1-274 Cl OMe SO₂Et 1-275 Cl OEt SO₂Me 1-276 Cl OEt SO₂Et1-277 Cl OiPr SO₂Me 1-278 Cl OiPr SO₂Et 1-279 Cl O(CH₂)₂OMe SO₂Me 1-280Cl O(CH₂)₄OMe SO₂Me 1-281 Cl O(CH₂)₄OMe SO₂Et 1-282 Cl O(CH₂)₃OMe SO₂Me1-283 Cl O(CH₂)₃OMe SO₂Et 1-284 Cl O(CH₂)₂OMe SO₂Me 1-285 Cl O(CH₂)₂OMeSO₂Et 1-286 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 1-287 Cl[1,4]dioxan-2-yl- SO₂Et methoxy 1-288 Cl OCH₂(CO)NMe₂ SO₂Me 1-289 ClOCH₂(CO)NMe₂ SO₂Et 1-290 Cl SMe SO₂Me 1-291 Cl SOMe SO₂Me 1-292 Br OMeBr 1-293 Br O(CH₂)₂OMe Br 1-294 Br O(CH₂)₂OMe SO₂Me 1-295 Br O(CH₂)₂OMeSO₂Et 1-296 Br O(CH₂)₃OMe SO₂Me 1-297 Br O(CH₂)₃OMe SO₂Et 1-298 BrO(CH₂)₄OMe SO₂Me 1-299 Br O(CH₂)₄OMe SO₂Et 1-300 Br [1,4]dioxan-2-yl-SO₂Me methoxy 1-301 Br [1,4]dioxan-2-yl- SO₂Et methoxy 1-302 IO(CH₂)₂OMe SO₂Me 1-303 I O(CH₂)₂OMe SO₂Et 1-304 I O(CH₂)₃OMe SO₂Me 1-305I O(CH₂)₃OMe SO₂Et 1-306 I O(CH₂)₄OMe SO₂Me 1-307 I O(CH₂)₄OMe SO₂Et1-308 I [1,4]dioxan-2-yl- SO₂Me methoxy 1-309 I [1,4]dioxan-2-yl- SO₂Etmethoxy 1-310 OMe SMe CF₃ 1-311 OMe SOMe CF₃ 1-312 OMe SO₂Me CF₃ 1-313OMe SOEt CF₃ 1-314 OMe SO₂Et CF₃ 1-315 OMe S(CH₂)₂OMe CF₃ 1-316 OMeSO(CH₂)₂OMe CF₃ 1-317 OMe SO₂(CH₂)₂OMe CF₃ 1-318 OMe SMe Cl 1-319 OMeSOMe Cl 1-320 OMe SO₂Me Cl 1-321 OMe SEt Cl 1-322 OMe SOEt Cl 1-323 OMeSO₂Et Cl 1-324 OMe S(CH₂)₂OMe Cl 1-325 OMe SO(CH₂)₂OMe Cl 1-326 OMeSO₂(CH₂)₂OMe Cl 1-327 OCH₂c-Pr SMe CF₃ 1-328 OCH₂c-Pr SOMe CF₃ 1-329OCH₂c-Pr SO₂Me CF₃ 1-330 OCH₂c-Pr SEt CF₃ 1-331 OCH₂c-Pr SOEt CF₃ 1-332OCH₂c-Pr SO₂Et CF₃ 1-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 1-334 OCH₂c-PrSO(CH₂)₂OMe CF₃ 1-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 1-336 OCH₂c-Pr SMe Cl1-337 OCH₂c-Pr SOMe Cl 1-338 OCH₂c-Pr SO₂Me Cl 1-339 OCH₂c-Pr SEt Cl1-340 OCH₂c-Pr SOEt Cl 1-341 OCH₂c-Pr SO₂Et Cl 1-342 OCH₂c-Pr S(CH₂)₂OMeCl 1-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 1-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 1-345OCH₂c-Pr SMe SO₂Me 1-346 OCH₂c-Pr SOMe SO₂Me 1-347 OCH₂c-Pr SO₂Me SO₂Me1-348 OCH₂c-Pr SEt SO₂Me 1-349 OCH₂c-Pr SOEt SO₂Me 1-350 OCH₂c-Pr SO₂EtSO₂Me 1-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 1-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me1-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 1-354 SO₂Me F CF₃ 1-355 SO₂Me NH₂ CF₃1-356 SO₂Me NHEt Cl 1-357 SMe SEt F 1-358 SMe SMe F 1-359 Cl SMe CF₃1-360 Cl S(O)Me CF₃ 1-361 Cl CF₃ CF₃ 1-362 Cl CF₃ CF₃

TABLE 2 Inventive compounds of the general formula (I) in which A is CYand R is methyl

Physical data No. X Y Z (¹H NMR, DMSO-d₆, 400 MHz) 2-1 F H Cl 2-2 F HSO₂Me 2-3 F H SO₂Et 2-4 F H CF₃ 2-5 F H NO₂ 2-6 Cl H Br 2-7 Cl H SMe 2-8Cl H SOMe 2-9 Cl H SO₂Me 2-10 Cl H SO₂CH₂Cl 2-11 Cl H SEt 2-12 Cl HSO₂Et 2-13 Cl H CF₃ 2-14 Cl H NO₂ 2-15 Cl H pyrazol-1-yl 2-16 Cl H1H-1,2,4-triazol-1-yl 2-17 Br H Cl 2-18 Br H Br 2-19 Br H SO₂Me 2-20 BrH SO₂Et 2-21 Br H CF₃ 2-22 SO₂Me H Cl 2-23 SO₂Me H Br 2-24 SO₂Me H SMe2-25 SO₂Me H SOMe 2-26 SO₂Me H SO₂Me 2-27 SO₂Me H SO₂Et 2-28 SO₂Me H CF₃2-29 SO₂Et H Cl 2-30 SO₂Et H Br 2-31 SO₂Et H SMe 2-32 SO₂Et H SOMe 2-33SO₂Et H SO₂Me 2-34 SO₂Et H CF₃ 2-35 NO₂ H F 2-36 NO₂ H Cl 2-37 NO₂ H Br2-38 NO₂ H I 2-39 NO₂ H CN 2-40 NO₂ H SO₂Me 2-41 NO₂ H SO₂Et 2-42 NO₂ HCF₃ 2-43 Me H Cl 2-44 Me H Br 2-45 Me H SMe 2-46 Me H SO₂Me 2-47 Me HSO₂CH₂Cl 2-48 Me H SEt 2-49 Me H SO₂Et 2-50 Me H CF₃ 2-51 CH₂SO₂Me H CF₃2-52 Et H Cl 2-53 Et H Br 2-54 Et H SMe 2-55 Et H SO₂Me 2-56 Et HSO₂CH₂Cl 2-57 Et H SEt 2-58 Et H SO₂Et 2-59 Et H CF₃ 2-60 CF₃ H Cl 2-61CF₃ H Br 2-62 CF₃ H SO₂Me 2-63 CF₃ H SO₂Et 2-64 CF₃ H CF₃ 2-65 NO₂ NH₂ F2-66 NO₂ NHMe F 2-67 NO₂ NMe₂ F 2-68 NO₂ Me Cl 2-69 NO₂ NH₂ Cl 2-70 NO₂NHMe Cl 2-71 NO₂ NMe₂ Cl 2-72 NO₂ NH₂ Br 2-73 NO₂ NHMe Br 2-74 NO₂ NMe₂Br 2-75 NO₂ NH₂ CF₃ 2-76 NO₂ NMe₂ CF₃ 2-77 NO₂ NH₂ SO₂Me 2-78 NO₂ NH₂SO₂Et 2-79 NO₂ NHMe SO₂Me 2-80 NO₂ NMe₂ SO₂Me 2-81 NO₂ NMe₂ SO₂Et 2-82NO₂ NH₂ 1H-1,2,4-triazol-1-yl 2-83 NO₂ NHMe 1H-1,2,4-triazol-1-yl 2-84NO₂ NMe₂ 1H-1,2,4-triazol-1-yl 2-85 Me SMe H 2-86 Me SOMe H 2-87 MeSO₂Me H 2-88 Me SEt H 2-89 Me SOEt H 2-90 Me SO₂Et H 2-91 Me S(CH₂)₂OMeH 2-92 Me SO(CH₂)₂OMe H 2-93 Me SO₂(CH₂)₂OMe H 2-94 Me F F 2-95 Me F Cl2-96 Me SEt F 2-97 Me SOEt F 2-98 Me SO₂Et F 2-99 Me Me Cl 2-100 Me F Cl12.08 (bs, 1H), 7.56 (dd, 1H), 7.43 (d, 1H), 2.44 (s, 3H), 2.32 (s, 3H)2-101 Me Cl Cl 2-102 Me NH₂ Cl 2-103 Me NHMe Cl 2-104 Me NMe₂ Cl 2-105Me O(CH₂)₂OMe Cl 2-106 Me O(CH₂)₃OMe Cl 2-107 Me O(CH₂)₄OMe Cl 2-108 MeOCH₂CONMe₂ Cl 2-109 Me O(CH₂)₂—CO—NMe₂ Cl 2-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl2-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 2-112 Me O(CH₂)₂—NHCO₂Me Cl 2-113 MeO—CH₂—NHSO₂cPr Cl 2-114 Me O(CH₂)-5-2,4-dimethyl-2,4- Cldihydro-3H-1,2,4-triazol-3-one 2-115 Me O(CH₂)-3,5-dimethyl- Cl1,2-oxazol-4-yl 2-116 Me SMe Cl 2-117 Me SOMe Cl 2-118 Me SO₂Me Cl 2-119Me SEt Cl 2-120 Me SOEt Cl 2-121 Me SO₂Et Cl 2-122 Me S(CH₂)₂OMe Cl2-123 Me SO(CH₂)₂OMe Cl 2-124 Me SO₂(CH₂)₂OMe Cl 2-125 Me NH₂ Br 2-126Me NHMe Br 2-127 Me NMe₂ Br 2-128 Me O(CH₂)CONEt₂ Br 2-129 MeO(CH₂)-5-pyrrolidin-2-one Br 2-130 Me SMe Br 2-131 Me SOMe Br 2-132 MeSO₂Me Br 2-133 Me SEt Br 2-134 Me SOEt Br 2-135 Me SO₂Et Br 2-136 Me SMeI 2-137 Me SOMe I 2-138 Me SO₂Me I 2-139 Me SEt I 2-140 Me SOEt I 2-141Me SO₂Et I 2-142 Me Cl CF₃ 2-143 Me SMe CF₃ 12.11 (bs, 1H), 7.77 (d,1H), 7.69 (d, 1H), 2.65 (s, 3H), 2.31 (s, 3H) 2-144 Me SOMe CF₃ 2-145 MeSO₂Me CF₃ 12.31 (bs, 1H), 8.02 (d, 1H), 7.97 (d, 1H), 3.42 (s, 3H), 2.71(s, 3H) 2-146 Me SEt CF₃ 2-147 Me SOEt CF₃ 2-148 Me SO₂Et CF₃ 2-149 MeS(CH₂)₂OMe CF₃ 2-150 Me SO(CH₂)₂OMe CF₃ 2-151 Me SO₂(CH₂)₂OMe CF₃ 2-152Me Me SO₂Me 2-153 Me 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 2-154 Me4,5-dihydro-1,2-oxazol-3-yl SO₂Et 2-155 Me 5-cyanomethyl-4,5-dihydro-SO₂Me 1,2-oxazol-3-yl 2-156 Me 5-cyanomethyl-4,5-dihydro- SO₂Et1,2-oxazol-3-yl 2-157 Me NH₂ SO₂Me 2-158 Me NHMe SO₂Me 2-159 Me NMe₂SO₂Me 2-160 Me NH(CH₂)₂OMe SO₂Me 2-161 Me pyrazol-1-yl SO₂Me 2-162 Me OHSO₂Me 2-163 Me OMe SO₂Me 2-164 Me OMe SO₂Et 2-165 Me OEt SO₂Me 2-166 MeOEt SO₂Et 2-167 Me OiPr SO₂Me 2-168 Me OiPr SO₂Et 2-169 Me O(CH₂)₂OMeSO₂Me 2-170 Me O(CH₂)₂OMe SO₂Et 2-171 Me O(CH₂)₃OMe SO₂Me 2-172 MeO(CH₂)₃OMe SO₂Et 2-173 Me O(CH₂)₄OMe SO₂Me 2-174 Me O(CH₂)₄OMe SO₂Et2-175 Me O(CH₂)₂NHSO₂Me SO₂Me 2-176 Me O(CH₂)₂NHSO₂Me SO₂Et 2-177 MeOCH₂(CO)NMe₂ SO₂Me 2-178 Me OCH₂(CO)NMe₂ SO₂Et 2-179 Me[1,4]dioxan-2-yl-methoxy SO₂Me 2-180 Me [1,4]dioxan-2-yl-methoxy SO₂Et2-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2-yl) 2-182 Me ClSO₂Me 2-183 Me SMe SO₂Me 2-184 Me SOMe SO₂Me 2-185 Me SO₂Me SO₂Me 12.36(bs, 1H), 8.27 (d, 1H), 8.02 (d, 1H), 3.59 (s, 3H), 3.56 (s, 3H), 2.68(s, 3H) 2-186 Me SO₂Me SO₂Et 2-187 Me SEt SO₂Me 2-188 Me SOEt SO₂Me2-189 Me SO₂Et SO₂Me 2-190 Me S(CH₂)₂OMe SO₂Me 2-191 Me SO(CH₂)₂OMeSO₂Me 2-192 Me SO₂(CH₂)₂OMe SO₂Me 2-193 CH₂SMe OMe SO₂Me 2-194 CH₂OMeOMe SO₂Me 2-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 2-196 CH₂O(CH₂)₂OMeNH(CH₂)₃OEt SO₂Me 2-197 CH₂O(CH₂)₃OMe OMe SO₂Me 2-198 CH₂O(CH₂)₂OMeNH(CH₂)₂OMe SO₂Me 2-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 2-200 Et SMe Cl2-201 Et SO₂Me Cl 2-202 Et SMe CF₃ 2-203 Et SO₂Me CF₃ 2-204 Et F SO₂Me2-205 Et NH(CH₂)₂OMe SO₂Me 2-206 iPr SO₂Me CF₃ 2-207 cPr SO₂Me CF₃ 2-208CF₃ O(CH₂)₂OMe F 2-209 CF₃ O(CH₂)₃OMe F 2-210 CF₃ OCH₂CONMe₂ F 2-211 CF₃[1,4]dioxan-2-yl-methoxy F 2-212 CF₃ O(CH₂)₂OMe Cl 2-213 CF₃ O(CH₂)₃OMeCl 2-214 CF₃ OCH₂CONMe₂ Cl 2-215 CF₃ [1,4]dioxan-2-yl-methoxy Cl 2-216CF₃ O(CH₂)₂OMe Br 2-217 CF₃ O(CH₂)₃OMe Br 2-218 CF₃ OCH₂CONMe₂ Br 2-219CF₃ [1,4]dioxan-2-yl-methoxy Br 2-220 CF₃ O(CH₂)₂OMe I 2-221 CF₃O(CH₂)₃OMe I 2-222 CF₃ OCH₂CONMe₂ I 2-223 CF₃ [1,4]dioxan-2-yl-methoxy I2-224 CF₃ F SO₂Me 2-225 CF₃ F SO₂Et 2-226 CF₃ O(CH₂)₂OMe SO₂Me 2-227 CF₃O(CH₂)₂OMe SO₂Et 2-228 CF₃ O(CH₂)₃OMe SO₂Me 2-229 CF₃ O(CH₂)₃OMe SO₂Et2-230 CF₃ OCH₂CONMe₂ SO₂Me 2-231 CF₃ OCH₂CONMe₂ SO₂Et 2-232 CF₃[1,4]dioxan-2-yl-methoxy SO₂Me 2-233 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Et2-234 F SMe CF₃ 2-235 F SOMe CF₃ 2-236 Cl Me Cl 2-237 Cl OCH₂CHCH₂ Cl2-238 Cl OCH₂CHF₂ Cl 2-239 Cl O(CH₂)₂OMe Cl 2-240 Cl OCH₂(CO)NMe₂ Cl13.63 (bs, 1H), 7.58 (2d, 2H), 4.70 (s, 2H), 3.00 (s, 3H), 2.86 (s, 3H)2-241 Cl O(CH₂)-5-pyrrolidin-2-one Cl 2-242 Cl SMe Cl 2-243 Cl SOMe Cl2-244 Cl SO₂Me Cl 2-245 Cl F SMe 2-246 Cl Cl SO₂Me 12.48 (bs,1H), 8.13(s, 1H), 7.89 (d, 1H), 3.30 (s, 3H) 2-247 Cl COOMe SO₂Me 2-248 Cl CONMe₂SO₂Me 2-249 Cl CONMe(OMe) SO₂Me 2-250 Cl CH₂OMe SO₂Me 2-251 Cl CH₂OMeSO₂Et 2-252 Cl CH₂OEt SO₂Me 2-253 Cl CH₂OEt SO₂Et 2-254 Cl CH₂OCH₂CHF₂SO₂Me 2-255 Cl CH₂OCH₂CF₃ SO₂Me 8.12 (d, 1H), 7.92 (d, 1H), 5.24 (s,2H), 4.30 (q, 2H) 2-256 Cl CH₂OCH₂CF₃ SO₂Et 2-257 Cl CH₂OCH₂CF₂CHF₂SO₂Me 2-258 Cl CH₂OcPentyl SO₂Me 2-259 Cl CH₂PO(OMe)₂ SO₂Me 2-260 Cl4,5-dihydro-1,2-oxazol-3-yl SMe 2-261 Cl 4,5-dihydro-1,2-oxazol-3-ylSO₂Me 2-262 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 2-263 Cl5-cyanomethyl-4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 2-264 Cl5-cyanomethyl-4,5-dihydro- SO₂Et 8.01 (d,1H), 7.92 (d, 1H), 5.19-1,2-oxazol-3-yl 5.13 (m, 1H), 3.64-3.54 (m, 1H), 3.39 (q, 2H), 3.12 (dd,1H), 3.05-2.96 (m, 3H), 1.15 (t, 3H) 2-265 Cl 5-(methoxymethyl)- SO₂Et4,5-dihydro-1,2-oxazol-3-yl 2-266 Cl 5-(methoxymethyl)-5-methyl- SO₂Et4,5-dihydro-1,2-oxazol-3-yl 2-267 Cl CH₂O-tetrahydrofuran-3-yl SO₂Me2-268 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et 2-269 ClCH₂OCH₂-tetrahydrofuran-2-yl SO₂Me 2-270 Cl CH₂OCH₂-tetrahydrofuran-2-ylSO₂Et 2-271 Cl CH₂OCH₂-tetrahydrofuran-3-yl SO₂Me 2-272 ClCH₂OCH₂-tetrahydrofuran-3-yl SO₂Et 2-273 Cl OMe SO₂Me 2-274 Cl OMe SO₂Et2-275 Cl OEt SO₂Me 2-276 Cl OEt SO₂Et 2-277 Cl OiPr SO₂Me 2-278 Cl OiPrSO₂Et 2-279 Cl O(CH₂)₂OMe SO₂Me 2-280 Cl O(CH₂)₄OMe SO₂Me 2-281 ClO(CH₂)₄OMe SO₂Et 2-282 Cl O(CH₂)₃OMe SO₂Me 2-283 Cl O(CH₂)₃OMe SO₂Et2-284 Cl O(CH₂)₂OMe SO₂Me 2-285 Cl O(CH₂)₂OMe SO₂Et 2-286 Cl[1,4]dioxan-2-yl-methoxy SO₂Me 2-287 Cl [1,4]dioxan-2-yl-methoxy SO₂Et2-288 Cl OCH₂(CO)NMe₂ SO₂Me 2-289 Cl OCH₂(CO)NMe₂ SO₂Et 2-290 Cl SMeSO₂Me 8.11 (d, 1H), 7.88 (d, 1H), 3.57 (s, 3H) 2-291 Cl SOMe SO₂Me 2-292Br OMe Br 2-293 Br O(CH₂)₂OMe Br 2-294 Br O(CH₂)₂OMe SO₂Me 2-295 BrO(CH₂)₂OMe SO₂Et 2-296 Br O(CH₂)₃OMe SO₂Me 2-297 Br O(CH₂)₃OMe SO₂Et2-298 Br O(CH₂)₄OMe SO₂Me 2-299 Br O(CH₂)₄OMe SO₂Et 2-300 Br[1,4]dioxan-2-yl-methoxy SO₂Me 2-301 Br [1,4]dioxan-2-yl-methoxy SO₂Et2-302 I O(CH₂)₂OMe SO₂Me 2-303 I O(CH₂)₂OMe SO₂Et 2-304 I O(CH₂)₃OMeSO₂Me 2-305 I O(CH₂)₃OMe SO₂Et 2-306 I O(CH₂)₄OMe SO₂Me 2-307 IO(CH₂)₄OMe SO₂Et 2-308 I [1,4]dioxan-2-yl-methoxy SO₂Me 2-309 I[1,4]dioxan-2-yl-methoxy SO₂Et 2-310 OMe SMe CF₃ 2-311 OMe SOMe CF₃2-312 OMe SO₂Me CF₃ 2-313 OMe SOEt CF₃ 2-314 OMe SO₂Et CF₃ 2-315 OMeS(CH₂)₂OMe CF₃ 2-316 OMe SO(CH₂)₂OMe CF₃ 2-317 OMe SO₂(CH₂)₂OMe CF₃2-318 OMe SMe Cl 2-319 OMe SOMe Cl 2-320 OMe SO₂Me Cl 2-321 OMe SEt Cl2-322 OMe SOEt Cl 2-323 OMe SO₂Et Cl 2-324 OMe S(CH₂)₂OMe Cl 2-325 OMeSO(CH₂)₂OMe Cl 2-326 OMe SO₂(CH₂)₂OMe Cl 2-327 OCH₂c-Pr SMe CF₃ 2-328OCH₂c-Pr SOMe CF₃ 2-329 OCH₂c-Pr SO₂Me CF₃ 2-330 OCH₂c-Pr SEt CF₃ 2-331OCH₂c-Pr SOEt CF₃ 2-332 OCH₂c-Pr SO₂Et CF₃ 2-333 OCH₂c-Pr S(CH₂)₂OMe CF₃2-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 2-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 2-336OCH₂c-Pr SMe Cl 2-337 OCH₂c-Pr SOMe Cl 2-338 OCH₂c-Pr SO₂Me Cl 2-339OCH₂c-Pr SEt Cl 2-340 OCH₂c-Pr SOEt Cl 2-341 OCH₂c-Pr SO₂Et Cl 2-342OCH₂c-Pr S(CH₂)₂OMe Cl 2-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 2-344 OCH₂c-PrSO₂(CH₂)₂OMe Cl 2-345 OCH₂c-Pr SMe SO₂Me 2-346 OCH₂c-Pr SOMe SO₂Me 2-347OCH₂c-Pr SO₂Me SO₂Me 2-348 OCH₂c-Pr SEt SO₂Me 2-349 OCH₂c-Pr SOEt SO₂Me2-350 OCH₂c-Pr SO₂Et SO₂Me 2-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 2-352OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 2-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 2-354 SO₂MeF CF₃ 2-355 SO₂Me NH₂ CF₃ 2-356 SO₂Me NHEt Cl 2-357 SMe SEt F 2-358 SMeSMe F 2-359 Cl SMe CF₃ 7.81 (s, 1H), 7.68 (d, 1H), 2.40 (s, 3H) 2-360 ClS(O)Me CF₃ 2-361 Cl SO₂Me CF₃ 2-362 Cl SO₂Me SO₂Me 12.55 (bs, 1H), 8.35(s, 1H), 8.21 (d, 1H), 3.66 (s, 3H), 3.56 (s, 3H)

TABLE 3 Inventive compounds of the general formula (I) in which A is CYand R is ethyl

Physical data No. X Y Z (¹H NMR, DMSO-d₆, 400 MHz) 3-1 F H Cl 3-2 F HSO₂Me 3-3 F H SO₂Et 3-4 F H CF₃ 3-5 F H NO₂ 3-6 Cl H Br 3-7 Cl H SMe 3-8Cl H SOMe 3-9 Cl H SO₂Me 12.55 (bs, 1H), 8.12 (s, 1H), 8.01 (d, 1H),7.92 (d, 1H), 3.35 (s, 3H), 2.84 (q, 2H), 1.26 (t, 3H) 3-10 Cl HSO₂CH₂Cl 3-11 Cl H SEt 3-12 Cl H SO₂Et 3-13 Cl H CF₃ 3-14 Cl H NO₂ 3-15Cl H pyrazol-1-yl 3-16 Cl H 1H-1,2,4-triazol-1-yl 3-17 Br H Cl 3-18 Br HBr 3-19 Br H SO₂Me 3-20 Br H SO₂Et 3-21 Br H CF₃ 3-22 SO₂Me H Cl 3-23SO₂Me H Br 3-24 SO₂Me H SMe 3-25 SO₂Me H SOMe 3-26 SO₂Me H SO₂Me 3-27SO₂Me H SO₂Et 3-28 SO₂Me H CF₃ 8.23 (d, 1H), 8.06 (s, 1H), 7.97 (d, 1H),2.85 (q, 2H), 1.24 (t, 3H) 3-29 SO₂Et H Cl 3-30 SO₂Et H Br 3-31 SO₂Et HSMe 3-32 SO₂Et H SOMe 3-33 SO₂Et H SO₂Me 3-34 SO₂Et H CF₃ 3-35 NO₂ H F3-36 NO₂ H Cl 3-37 NO₂ H Br 3-38 NO₂ H I 3-39 NO₂ H CN 3-40 NO₂ H SO₂Me3-41 NO₂ H SO₂Et 3-42 NO₂ H CF₃ 8.53 (s, 1H), 8.29 (d, 1H), 8.08 (d,1H), 2.32 (q, 2H), 1.23 (t, 3H) 3-43 Me H Cl 3-44 Me H Br 3-45 Me H SMe3-46 Me H SO₂Me 3-47 Me H SO₂CH₂Cl 3-48 Me H SEt 3-49 Me H SO₂Et 3-50 MeH CF₃ 3-51 CH₂SO₂Me H CF₃ 3-52 Et H Cl 3-53 Et H Br 3-54 Et H SMe 3-55Et H SO₂Me 3-56 Et H SO₂CH₂Cl 3-57 Et H SEt 3-58 Et H SO₂Et 3-59 Et HCF₃ 3-60 CF₃ H Cl 3-61 CF₃ H Br 3-62 CF₃ H SO₂Me 3-63 CF₃ H SO₂Et 3-64CF₃ H CF₃ 3-65 NO₂ NH₂ F 3-66 NO₂ NHMe F 3-67 NO₂ NMe₂ F 3-68 NO₂ Me Cl3-69 NO₂ NH₂ Cl 3-70 NO₂ NHMe Cl 3-71 NO₂ NMe₂ Cl 3-72 NO₂ NH₂ Br 3-73NO₂ NHMe Br 3-74 NO₂ NMe₂ Br 3-75 NO₂ NH₂ CF₃ 3-76 NO₂ NMe₂ CF₃ 3-77 NO₂NH₂ SO₂Me 3-78 NO₂ NH₂ SO₂Et 3-79 NO₂ NHMe SO₂Me 3-80 NO₂ NMe₂ SO₂Me3-81 NO₂ NMe₂ SO₂Et 3-82 NO₂ NH₂ 1H-1,2,4-triazol-1-yl 3-83 NO₂ NHMe1H-1,2,4-triazol-1-yl 3-84 NO₂ NMe₂ 1H-1,2,4-triazol-1-yl 3-85 Me SMe H3-86 Me SOMe H 3-87 Me SO₂Me H 3-88 Me SEt H 3-89 Me SOEt H 3-90 MeSO₂Et H 3-91 Me S(CH₂)₂OMe H 3-92 Me SO(CH₂)₂OMe H 3-93 Me SO₂(CH₂)₂OMeH 3-94 Me F F 3-95 Me F Cl 3-96 Me SEt F 3-97 Me SOEt F 3-98 Me SO₂Et F3-99 Me Me Cl 3-100 Me F Cl 3-101 Me Cl Cl 3-102 Me NH₂ Cl 3-103 Me NHMeCl 3-104 Me NMe₂ Cl 3-105 Me O(CH₂)₂OMe Cl 3-106 Me O(CH₂)₃OMe Cl 3-107Me O(CH₂)₄OMe Cl 3-108 Me OCH₂CONMe₂ Cl 3-109 Me O(CH₂)₂—CONMe₂ Cl 3-110Me O(CH₂)₂—NH(CO)NMe₂ Cl 3-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 3-112 MeO(CH₂)₂NHCO₂Me Cl 3-113 Me OCH₂NHSO₂cPr Cl 3-114 MeO(CH₂)-5-2,4-di-methyl- Cl 2,4-dihydro-3H-1,2,4-triazol-3-one 3-115 MeO(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 3-116 Me SMe Cl 3-117 Me SOMe Cl3-118 Me SO₂Me Cl 3-119 Me SEt Cl 3-120 Me SOEt Cl 3-121 Me SO₂Et Cl3-122 Me S(CH₂)₂OMe Cl 3-123 Me SO(CH₂)₂OMe Cl 3-124 Me SO₂(CH₂)₂OMe Cl3-125 Me NH₂ Br 3-126 Me NHMe Br 3-127 Me NMe₂ Br 3-128 Me OCH₂CONMe₂ Br3-129 Me O(CH₂)-5-pyrrolidin-2-one Br 3-130 Me SMe Br 3-131 Me SOMe Br3-132 Me SO₂Me Br 3-133 Me SEt Br 3-134 Me SOEt Br 3-135 Me SO₂Et Br3-136 Me SMe I 3-137 Me SOMe I 3-138 Me SO₂Me I 3-139 Me SEt I 3-140 MeSOEt I 3-141 Me SO₂Et I 3-142 Me Cl CF₃ 3-143 Me SMe CF₃ 11.84 (s, 1H),7.99 (d, 1H), 7.87 (d, 1H), 3.30 (q, 2H), 2.94 (s, 3H), 2.44 (s, 3H),1.09 (t, 3H) 3-144 Me SOMe CF₃ 3-145 Me SO₂Me CF₃ 7.87 (2d, 2H), 3.36(s, 3H), 2.70 (q, 2H), 2.08 (s, 3H), 1.23 (t, 3H) 3-146 Me SEt CF₃ 3-147Me SOEt CF₃ 3-148 Me SO₂Et CF₃ 3-149 Me S(CH₂)₂OMe CF₃ 3-150 MeSO(CH₂)₂OMe CF₃ 3-151 Me SO₂(CH₂)₂OMe CF₃ 3-152 Me Me SO₂Me 3-153 Me4,5-dihydro-1,2-oxazol-3-yl SO₂Me 3-154 Me 4,5-dihydro-1,2-oxazol-3-ylSO₂Et 3-155 Me 5-cyanomethyl-4,5-dihydro- SO₂Me 1,2-oxazol-3-yl 3-156 Me5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 3-157 Me NH₂ SO₂Me3-158 Me NHMe SO₂Me 3-159 Me NMe₂ SO₂Me 3-160 Me NH(CH₂)₂OMe SO₂Me 3-161Me pyrazol-1-yl SO₂Me 3-162 Me OH SO₂Me 3-163 Me OMe SO₂Me 3-164 Me OMeSO₂Et 3-165 Me OEt SO₂Me 3-166 Me OEt SO₂Et 3-167 Me OiPr SO₂Me 3-168 MeOiPr SO₂Et 3-169 Me O(CH₂)₂OMe SO₂Me 3-170 Me O(CH₂)₂OMe SO₂Et 3-171 MeO(CH₂)₃OMe SO₂Me 3-172 Me O(CH₂)₃OMe SO₂Et 3-173 Me O(CH₂)₄OMe SO₂Me3-174 Me O(CH₂)₄OMe SO₂Et 3-175 Me O(CH₂)₂NHSO₂Me SO₂Me 3-176 MeO(CH₂)₂NHSO₂Me SO₂Et 3-177 Me OCH₂(CO)NMe₂ SO₂Me 3-178 Me OCH₂(CO)NMe₂SO₂Et 3-179 Me [1,4]dioxan-2-yl-methoxy SO₂Me 3-180 Me[1,4]dioxan-2-yl-methoxy SO₂Et 3-181 Me O(CH₂)₂—O—(3,5- SO₂Medimethoxypyrimidin-2-yl) 3-182 Me Cl SO₂Me 3-183 Me SMe SO₂Me 3-184 MeSOMe SO₂Me 3-185 Me SO₂Me SO₂Me 12.30 (bs, 1H), 8.24 (d, 1H), 8.03 (d,1H), 3.59 (s, 3H), 3.56 (s, 3H), 2.85 (q, 2H), 2.68 (s, 3H), 1.26 (t,3H) 3-186 Me SO₂Me SO₂Et 3-187 Me SEt SO₂Me 3-188 Me SOEt SO₂Me 3-189 MeSO₂Et SO₂Me 3-190 Me S(CH₂)₂OMe SO₂Me 3-191 Me SO(CH₂)₂OMe SO₂Me 3-192Me SO₂(CH₂)₂OMe SO₂Me 3-193 CH₂SMe OMe SO₂Me 3-194 CH₂OMe OMe SO₂Me3-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 3-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEtSO₂Me 3-197 CH₂O(CH₂)₃OMe OMe SO₂Me 3-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMeSO₂Me 3-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 3-200 Et SMe Cl 3-201 EtSO₂Me Cl 3-202 Et SMe CF₃ 3-203 Et SO₂Me CF₃ 3-204 Et F SO₂Me 3-205 EtNH(CH₂)₂OMe SO₂Me 3-206 iPr SO₂Me CF₃ 3-207 cPr SO₂Me CF₃ 3-208 CF₃O(CH₂)₂OMe F 3-209 CF₃ O(CH₂)₃OMe F 3-210 CF₃ OCH₂CONMe₂ F 3-211 CF₃[1,4]dioxan-2-yl-methoxy F 3-212 CF₃ O(CH₂)₂OMe Cl 3-213 CF₃ O(CH₂)₃OMeCl 3-214 CF₃ OCH₂CONMe₂ Cl 3-215 CF₃ [1,4]dioxan-2-yl-methoxy Cl 3-216CF₃ O(CH₂)₂OMe Br 3-217 CF₃ O(CH₂)₃OMe Br 3-218 CF₃ OCH₂CONMe₂ Br 3-219CF₃ [1,4]dioxan-2-yl-methoxy Br 3-220 CF₃ O(CH₂)₂OMe I 3-221 CF₃O(CH₂)₃OMe I 3-222 CF₃ OCH₂CONMe₂ I 3-223 CF₃ [1,4]dioxan-2-yl-methoxy I3-224 CF₃ F SO₂Me 3-225 CF₃ F SO₂Et 3-226 CF₃ O(CH₂)₂OMe SO₂Me 3-227 CF₃O(CH₂)₂OMe SO₂Et 3-228 CF₃ O(CH₂)₃OMe SO₂Me 3-229 CF₃ O(CH₂)₃OMe SO₂Et3-230 CF₃ OCH₂CONMe₂ SO₂Me 3-231 CF₃ OCH₂CONMe₂ SO₂Et 3-232 CF₃[1,4]dioxan-2-yl-methoxy SO₂Me 3-233 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Et3-234 F SMe CF₃ 3-235 F SOMe CF₃ 8.15 (d, 1H), 7.33 (d, 1H), 2.18 (q,2H), 1.04 (t, 3H) 3-236 Cl Me Cl 3-237 Cl OCH₂CHCH₂ Cl 3-238 Cl OCH₂CHF₂Cl 3-239 Cl O(CH₂)₂OMe Cl 3-240 Cl OCH₂(CO)NMe₂ Cl 3-241 ClO(CH₂)-5-pyrrolidin-2-one Cl 3-242 Cl SMe Cl 3-243 Cl SOMe Cl 3-244 ClSO2Me Cl 3-245 Cl F SMe 3-246 Cl Cl SO₂Me 8.12 (d, 1H), 7.89 (s, 1H),3.47 (s, 3H), 2.84 (q, 2H), 1.26 (t, 3H) 3-247 Cl COOMe SO₂Me 3-248 ClCONMe₂ SO₂Me 3-249 Cl CONMe(OMe) SO₂Me 3-250 Cl CH₂OMe SO₂Me 3-251 ClCH₂OMe SO₂Et 3-252 Cl CH₂OEt SO₂Me 3-253 Cl CH₂OEt SO₂Et 3-254 ClCH₂OCH₂CHF₂ SO₂Me 3-255 Cl CH₂OCH₂CF₃ SO₂Me 8.16 (d, 1H), 7.66 (d, 1H),5.36 (s, 2H), 4.04 (q, 2H), 3.22 (s, 3H), 2.58 (s, 2H), 1.22 (t, 3H)3-256 Cl CH₂OCH₂CF₃ SO₂Et 3-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 3-258 ClCH₂OcPentyl SO₂Me 3-259 Cl CH₂PO(OMe)₂ SO₂Me 3-260 Cl4,5-dihydro-1,2-oxazol-3-yl SMe 3-261 Cl 4,5-dihydro-1,2-oxazol-3-ylSO₂Me 3-262 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 3-263 Cl5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl SO₂Me 3-264 Cl5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl SO₂Et 8.08 (d, 1H), 8.02 (d,1H), 5.10- 5.20 (m, 1H), 3.39 (q, 3H), 3.14 (dd, 1H), 3.02-2.97 (m, 2H),2.82 (q, 2H), 1.24 (t, 3H), 1.15 (t, 3H) 3-265 Cl5-(methoxymethyl)-4,5-dihydro- SO₂Et 1,2-oxazol-3-yl 3-266 Cl5-(methoxymethyl)-5-methyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 3-267 ClCH₂O-tetrahydrofuran-3-yl SO₂Me 3-268 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et3-269 Cl CH₂OCH₂-tetrahydrofuran-2-yl SO₂Me 3-270 ClCH₂OCH₂-tetrahydrofuran-2-yl SO₂Et 3-271 Cl CH₂OCH₂-tetrahydrofuran-3-ylSO₂Me 3-272 Cl CH₂OCH₂-tetrahydrofuran-3-yl SO₂Et 3-273 Cl OMe SO₂Me3-274 Cl OMe SO₂Et 3-275 Cl OEt SO₂Me 3-276 Cl OEt SO₂Et 3-277 Cl OiPrSO₂Me 3-278 Cl OiPr SO₂Et 3-279 Cl O(CH₂)₂OMe SO₂Me 3-280 Cl O(CH₂)₄OMeSO₂Me 3-281 Cl O(CH₂)₄OMe SO₂Et 3-282 Cl O(CH₂)₃OMe SO₂Me 3-283 ClO(CH₂)₃OMe SO₂Et 3-284 Cl O(CH₂)₂OMe SO₂Me 3-285 Cl O(CH₂)₂OMe SO₂Et3-286 Cl [1,4]dioxan-2-yl-methoxy SO₂Me 3-287 Cl[1,4]dioxan-2-yl-methoxy SO₂Et 3-288 Cl OCH₂(CO)NMe₂ SO₂Me 3-289 ClOCH₂(CO)NMe₂ SO₂Et 3-290 Cl SMe SO₂Me 12.43 (bs, 1H), 8.11 (d, 1H), 7.89(d, 1H), 3.57 (s, 3H), 2.86 (q, 2H), 1.26 (t, 3H) 3-291 Cl SOMe SO₂Me3-292 Br OMe Br 3-293 Br O(CH₂)₂OMe Br 3-294 Br O(CH₂)₂OMe SO₂Me 3-295Br O(CH₂)₂OMe SO₂Et 3-296 Br O(CH₂)₃OMe SO₂Me 3-297 Br O(CH₂)₃OMe SO₂Et3-298 Br O(CH₂)₄OMe SO₂Me 3-299 Br O(CH₂)₄OMe SO₂Et 3-300 Br[1,4]dioxan-2-yl-methoxy SO₂Me 3-301 Br [1,4]dioxan-2-yl-methoxy SO₂Et3-302 I O(CH₂)₂OMe SO₂Me 3-303 I O(CH₂)₂OMe SO₂Et 3-304 I O(CH₂)₃OMeSO₂Me 3-305 I O(CH₂)₃OMe SO₂Et 3-306 I O(CH₂)₄OMe SO₂Me 3-307 IO(CH₂)₄OMe SO₂Et 3-308 I [1,4]dioxan-2-yl-methoxy SO₂Me 3-309 I[1,4]dioxan-2-yl-methoxy SO₂Et 3-310 OMe SMe CF₃ 3-311 OMe SOMe CF₃3-312 OMe SO₂Me CF₃ 3-313 OMe SOEt CF₃ 3-314 OMe SO₂Et CF₃ 3-315 OMeS(CH₂)₂OMe CF₃ 3-316 OMe SO(CH₂)₂OMe CF₃ 3-317 OMe SO₂(CH₂)₂OMe CF₃3-318 OMe SMe Cl 3-319 OMe SOMe Cl 3-320 OMe SO₂Me Cl 3-321 OMe SEt Cl3-322 OMe SOEt Cl 3-323 OMe SO₂Et Cl 3-324 OMe S(CH₂)₂OMe Cl 3-325 OMeSO(CH₂)₂OMe Cl 3-326 OMe SO₂(CH₂)₂OMe Cl 3-327 OCH₂c-Pr SMe CF₃ 3-328OCH₂c-Pr SOMe CF₃ 3-329 OCH₂c-Pr SO₂Me CF₃ 3-330 OCH₂c-Pr SEt CF₃ 3-331OCH₂c-Pr SOEt CF₃ 3-332 OCH₂c-Pr SO₂Et CF₃ 3-333 OCH₂c-Pr S(CH₂)₂OMe CF₃3-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 3-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 3-336OCH₂c-Pr SMe Cl 3-337 OCH₂c-Pr SOMe Cl 3-338 OCH₂c-Pr SO₂Me Cl 3-339OCH₂c-Pr SEt Cl 3-340 OCH₂c-Pr SOEt Cl 3-341 OCH₂c-Pr SO₂Et Cl 3-342OCH₂c-Pr S(CH₂)₂OMe Cl 3-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 3-344 OCH₂c-PrSO₂(CH₂)₂OMe Cl 3-345 OCH₂c-Pr SMe SO₂Me 3-346 OCH₂c-Pr SOMe SO₂Me 3-347OCH₂c-Pr SO₂Me SO₂Me 3-348 OCH₂c-Pr SEt SO₂Me 3-349 OCH₂c-Pr SOEt SO₂Me3-350 OCH₂c-Pr SO₂Et SO₂Me 3-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 3-352OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 3-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 3-354 SO₂MeF CF₃ 3-355 SO₂Me NH₂ CF₃ 3-356 SO₂Me NHEt Cl 3-357 SMe SEt F 3-358 SMeSMe F 3-359 Cl SMe CF₃ 12.39 (bs, 1H), 7.95 (d, 1H), 7.85 (d, 1H), 2.86(q, 2H), 1.27 (t, 3H) 3-360 Cl S(O)Me CF₃ 3-361 Cl SO₂Me CF₃ 12.54 (bs,1H), 8.17 (d, 1H), 8.15 (d, 1H), 3.52 (s, 3H), 2.85 (q, 2H), 1.27 (t,3H) 3-362 Cl SO₂Me SO₂Me

TABLE 4 Inventive compounds of the general formula (I) in which A is CYand R is trifluoromethyl

Physical data No. X Y Z (¹H NMR, DMSO-d₆, 400 MHz) 4-1 F H Cl 4-2 F HSO₂Me 4-3 F H SO₂Et 4-4 F H CF₃ 4-5 F H NO₂ 4-6 Cl H Br 4-7 Cl H SMe 4-8Cl H SOMe 4-9 Cl H SO₂Me 13.22 (bs, 1H), 8.15 (s, 1H), 8.04 (d, 1H),7.95 (d, 1H) 4-10 Cl H SO₂CH₂Cl 4-11 Cl H SEt 4-12 Cl H SO₂Et 4-13 Cl HCF₃ 4-14 Cl H NO₂ 4-15 Cl H pyrazol-1-yl 4-16 Cl H 1H-1,2,4-triazol-1-yl 4-17 Br H Cl 4-18 Br H Br 4-19 Br H SO₂Me 4-20 Br H SO₂Et 4-21 Br HCF₃ 4-22 SO₂Me H Cl 4-23 SO₂Me H Br 4-24 SO₂Me H SMe 4-25 SO₂Me H SOMe4-26 SO₂Me H SO₂Me 4-27 SO₂Me H SO₂Et 4-28 SO₂Me H CF₃ 8.33 (d, 1H),8.29 (s, 1H), 8.06 (d, 1H), 3.46 (s, 3H) 4-29 SO₂Et H Cl 4-30 SO₂Et H Br4-31 SO₂Et H SMe 4-32 SO₂Et H SOMe 4-33 SO₂Et H SO₂Me 4-34 SO₂Et H CF₃4-35 NO₂ H F 4-36 NO₂ H Cl 4-37 NO₂ H Br 4-38 NO₂ H I 4-39 NO₂ H CN 4-40NO₂ H SO₂Me 4-41 NO₂ H SO₂Et 4-42 NO₂ H CF₃ 4-43 Me H Cl 4-44 Me H Br4-45 Me H SMe 4-46 Me H SO₂Me 4-47 Me H SO₂CH₂Cl 4-48 Me H SEt 4-49 Me HSO₂Et 4-50 Me H CF₃ 4-51 CH₂SO₂Me H CF₃ 4-52 Et H Cl 4-53 Et H Br 4-54Et H SMe 4-55 Et H SO₂Me 4-56 Et H SO₂CH₂Cl 4-57 Et H SEt 4-58 Et HSO₂Et 4-59 Et H CF₃ 4-60 CF₃ H Cl 4-61 CF₃ H Br 4-62 CF₃ H SO₂Me 4-63CF₃ H SO₂Et 4-64 CF₃ H CF₃ 4-65 NO₂ NH₂ F 4-66 NO₂ NHMe F 4-67 NO₂ NMe₂F 4-68 NO₂ Me Cl 4-69 NO₂ NH₂ Cl 4-70 NO₂ NHMe Cl 4-71 NO₂ NMe₂ Cl 4-72NO₂ NH₂ Br 4-73 NO₂ NHMe Br 4-74 NO₂ NMe₂ Br 4-75 NO₂ NH₂ CF₃ 4-76 NO₂NMe₂ CF₃ 4-77 NO₂ NH₂ SO₂Me 4-78 NO₂ NH₂ SO₂Et 4-79 NO₂ NHMe SO₂Me 4-80NO₂ NMe₂ SO₂Me 4-81 NO₂ NMe₂ SO₂Et 4-82 NO₂ NH₂ 1H-1,2,4-triazol- 1-yl4-83 NO₂ NHMe 1H-1,2,4-triazol- 1-yl 4-84 NO₂ NMe₂ 1H-1,2,4-triazol-1-yl 4-85 Me SMe H 4-86 Me SOMe H 4-87 Me SO₂Me H 4-88 Me SEt H 4-89 MeSOEt H 4-90 Me SO₂Et H 4-91 Me S(CH₂)₂OMe H 4-92 Me SO(CH₂)₂OMe H 4-93Me SO₂(CH₂)₂OMe H 4-94 Me F F 4-95 Me F Cl 4-96 Me SEt F 4-97 Me SOEt F4-98 Me SO₂Et F 4-99 Me Me Cl 4-100 Me F Cl 4-101 Me Cl Cl 4-102 Me NH₂Cl 4-103 Me NHMe Cl 4-104 Me NMe₂ Cl 4-105 Me O(CH₂)₂OMe Cl 4-106 MeO(CH₂)₃OMe Cl 4-107 Me O(CH₂)₄OMe Cl 4-108 Me OCH₂CONMe₂ Cl 4-109 MeO(CH₂)₂—CO—NMe₂ Cl 4-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 4-111 Me O(CH₂)₂— ClNH(CO)NHCO₂Et 4-112 Me O(CH₂)₂—NHCO₂Me Cl 4-113 Me OCH₂—NHSO₂cPr Cl4-114 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one4-115 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 4-116 Me SMe Cl 4-117Me SOMe Cl 4-118 Me SO₂Me Cl 4-119 Me SEt Cl 4-120 Me SOEt Cl 4-121 MeSO₂Et Cl 4-122 Me S(CH₂)₂OMe Cl 4-123 Me SO(CH₂)₂OMe Cl 4-124 MeSO₂(CH₂)₂OMe Cl 4-125 Me NH₂ Br 4-126 Me NHMe Br 4-127 Me NMe₂ Br 4-128Me OCH₂(CO)NMe₂ Br 4-129 Me O(CH₂)-5-pyrrolidin-2- Br one 4-130 Me SMeBr 4-131 Me SOMe Br 4-132 Me SO₂Me Br 4-133 Me SEt Br 4-134 Me SOEt Br4-135 Me SO₂Et Br 4-136 Me SMe I 4-137 Me SOMe I 4-138 Me SO₂Me I 4-139Me SEt I 4-140 Me SOEt I 4-141 Me SO₂Et I 4-142 Me Cl CF₃ 4-143 Me SMeCF₃ 7.72 (d, 1H), 7.65 (d, 1H), 2.67 (s, 3H), 2.30 (s, 3H) 4-144 Me SOMeCF₃ 7.89 (d, 1H), 7.85 (d, 1H), 3.05 (s, 3H), 2.85 (s, 3H) 4-145 MeSO₂Me CF₃ 13.11 (bs, 1H), 8.05 (d, 1H), 7.99 (d, 1H), 3.43 (s, 3H), 2.73(s, 3H) 4-146 Me SEt CF₃ 4-147 Me SOEt CF₃ 4-148 Me SO₂Et CF₃ 4-149 MeS(CH₂)₂OMe CF₃ 4-150 Me SO(CH₂)₂OMe CF₃ 4-151 Me SO₂(CH₂)₂OMe CF₃ 4-152Me Me SO₂Me 4-153 Me 4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 4-154 Me4,5-dihydro-1,2-oxazol- SO₂Et 3-yl 4-155 Me 5-cyanomethyl-4,5- SO₂Medihydro-1,2-oxazol-3-yl 4-156 Me 5-cyanomethyl-4,5- SO₂Etdihydro-1,2-oxazol-3-yl 4-157 Me NH₂ SO₂Me 4-158 Me NHMe SO₂Me 4-159 MeNMe₂ SO₂Me 4-160 Me NH(CH₂)₂OMe SO₂Me 4-161 Me pyrazol-1-yl SO₂Me 4-162Me OH SO₂Me 4-163 Me OMe SO₂Me 4-164 Me OMe SO₂Et 4-165 Me OEt SO₂Me4-166 Me OEt SO₂Et 4-167 Me OiPr SO₂Me 4-168 Me OiPr SO₂Et 4-169 MeO(CH₂)₂OMe SO₂Me 4-170 Me O(CH₂)₂OMe SO₂Et 4-171 Me O(CH₂)₃OMe SO₂Me4-172 Me O(CH₂)₃OMe SO₂Et 4-173 Me O(CH₂)₄OMe SO₂Me 4-174 Me O(CH₂)₄OMeSO₂Et 4-175 Me O(CH₂)₂NHSO2Me SO₂Me 4-176 Me O(CH₂)₂NHSO2Me SO₂Et 4-177Me OCH₂(CO)NMe₂ SO₂Me 4-178 Me OCH₂(CO)NMe₂ SO₂Et 4-179 Me[1,4]dioxan-2-yl- SO₂Me methoxy 4-180 Me [1,4]dioxan-2-yl- SO₂Et methoxy4-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2-yl) 4-182 Me ClSO₂Me 13.09 (bs, 1H), 8.05 (d, 1H), 7.77 (d, 1H), 3.44 (s, 3H), 2.47 (s,3H) 4-183 Me SMe SO₂Me 4-184 Me SOMe SO₂Me 4-185 Me SO₂Me SO₂Me 4-186 MeSO₂Me SO₂Et 4-187 Me SEt SO₂Me 4-188 Me SOEt SO₂Me 4-189 Me SO₂Et SO₂Me4-190 Me S(CH₂)₂OMe SO₂Me 4-191 Me SO(CH₂)₂OMe SO₂Me 4-192 MeSO₂(CH₂)₂OMe SO2Me 4-193 CH₂SMe OMe SO₂Me 4-194 CH₂OMe OMe SO₂Me 4-195CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 4-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me4-197 CH₂O(CH₂)₂OMe OMe SO₂Me 4-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me4-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 4-200 Et SMe Cl 4-201 Et SO₂Me Cl4-202 Et SMe CF₃ 4-203 Et SO₂Me CF₃ 4-204 Et F SO₂Me 4-205 EtNH(CH₂)₂OMe SO₂Me 4-206 iPr SO₂Me CF₃ 4-207 cPr SO₂Me CF₃ 4-208 CF₃O(CH₂)₂OMe F 4-209 CF₃ O(CH₂)₃OMe F 4-210 CF₃ OCH₂CONMe₂ F 4-211 CF₃[1,4]dioxan-2-yl- F methoxy 4-212 CF₃ O(CH₂)₂OMe Cl 4-213 CF₃ O(CH₂)₃OMeCl 4-214 CF₃ OCH₂CONMe₂ Cl 4-215 CF₃ [1,4]dioxan-2-yl- Cl methoxy 4-216CF₃ O(CH₂)₂OMe Br 4-217 CF₃ O(CH₂)₃OMe Br 4-218 CF₃ OCH₂CONMe₂ Br 4-219CF₃ [1,4]dioxan-2-yl- Br methoxy 4-220 CF₃ O(CH₂)₂OMe I 4-221 CF₃O(CH₂)₃OMe I 4-222 CF₃ OCH₂CONMe₂ I 4-223 CF₃ [1,4]dioxan-2-yl- Imethoxy 4-224 CF₃ F SO₂Me 4-225 CF₃ F SO₂Et 4-226 CF₃ O(CH₂)₂OMe SO₂Me4-227 CF₃ O(CH₂)₂OMe SO₂Et 4-228 CF₃ O(CH₂)₃OMe SO₂Me 4-229 CF₃O(CH₂)₃OMe SO₂Et 4-230 CF₃ OCH₂CONMe₂ SO₂Me 4-231 CF₃ OCH₂CONMe₂ SO₂Et4-232 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 4-233 CF₃ [1,4]dioxan-2-yl-SO₂Et methoxy 4-234 F SMe CF₃ 4-235 F SOMe CF₃ 4-236 Cl Me Cl 4-237 ClOCH₂CHCH₂ Cl 4-238 Cl OCH₂CHF₂ Cl 4-239 Cl O(CH₂)₂OMe Cl 4-240 ClOCH₂CONMe₂ Cl 13.08 (bs, 1H), 7.67 (d, 1H), 7.48 (d, 1H), 4.74 (s, 2H),3.01 (s, 3H), 2.87 (s, 3H) 4-241 Cl O(CH₂)-5-pyrrolidin-2- Cl one 4-242Cl SMe Cl 4-243 Cl SOMe Cl 4-244 Cl SO₂Me Cl 4-245 Cl F SMe 4-246 Cl ClSO₂Me 13.29 (bs, 1H), 8.18 (d, 1H), 7.91 (d, 1H), 3.49 (s, 3H) 4-247 ClCOOMe SO₂Me 4-248 Cl CONMe₂ SO₂Me 4-249 Cl CONMe(OMe) SO₂Me 4-250 ClCH₂OMe SO₂Me 4-251 Cl CH₂OMe SO₂Et 4-252 Cl CH₂OEt SO₂Me 4-253 Cl CH₂OEtSO₂Et 4-254 Cl CH₂OCH₂CHF₂ SO₂Me 4-255 Cl CH₂OCH₂CF₃ SO₂Me 13.21 (bs,1H), 8.11 (d, 1H), 7.95 (d, 1H), 5.25 (s, 2H), 4.29 (q, 2H), 4-256 ClCH₂OCH₂CF₃ SMe 12.98 (bs, 1H), 7.64 (d, 1H), 7.44 (d, 1H), 4.90 (s, 2H),4.18 (q, 2H), 2.57 (s, 3H) 4-257 Cl CH₂OCH₂CF₃ SO₂Et 4-258 ClCH₂OCH₂CF₂CHF₂ SO₂Me 4-259 Cl CH₂OcPentyl SO₂Me 4-260 Cl CH₂PO(OMe)₂SO₂Me 4-261 Cl 4,5-dihydro-1,2-oxazol- SMe 3-yl 4-262 Cl4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 4-263 Cl 4,5-dihydro-1,2-oxazol-SO₂Et 3-yl 4-264 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl4-265 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-266 Cl5-(methoxymethyl)-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-267 Cl5-(methoxymethyl)-5- SO₂Et methyl-4,5-dihydro-1,2- oxazol-3-yl 4-268 ClCH₂O-tetrahydrofuran- SO₂Me 3-yl 4-269 Cl CH₂O-tetrahydrofuran- SO₂Et3-yl 4-270 Cl CH₂OCH₂- SO₂Me 13.24 (bs, 1H), 8.11 (d, 1H), 7.91tetrahydrofuran-2-yl (d, 1H), 5.09 (dd, 2H), 4.02-3.93 (m, 1H), 3.72(dd, 1H), 3.62 (dd, 1H), 3.59-3.52 (m, 3H), 1.93-1.86 (m, 1H), 1.83-1.75(m, 2H), 1.59- 1.51 (m, 1H) 4-271 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl4-272 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 4-273 Cl CH₂OCH₂- SO₂Ettetrahydrofuran-3-yl 4-274 Cl OMe SO₂Me 4-275 Cl OMe SO₂Et 4-276 Cl OEtSO₂Me 4-277 Cl OEt SO₂Et 4-278 Cl OiPr SO₂Me 4-279 Cl OiPr SO₂Et 4-280Cl O(CH₂)₂OMe SO₂Me 4-281 Cl O(CH₂)₄OMe SO₂Me 4-282 Cl O(CH₂)₄OMe SO₂Et4-283 Cl O(CH₂)₃OMe SO₂Me 4-284 Cl O(CH₂)₃OMe SO₂Et 4-285 Cl O(CH₂)₂OMeSO₂Me 4-286 Cl O(CH₂)₂OMe SO₂Et 4-287 Cl [1,4]dioxan-2-yl- SO₂Me methoxy4-288 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 4-289 Cl OCH₂(CO)NMe₂ SO₂Me4-290 Cl OCH₂(CO)NMe₂ SO₂Et 4-291 Cl SMe SO₂Me 13.22 (bs, 1H), 8.14 (d,1H), 7.91 (d, 1H), 3.59 (s, 3H) 4-292 Cl SOMe SO₂Me 4-293 Br OMe Br4-294 Br O(CH₂)₂OMe Br 4-295 Br O(CH₂)₂OMe SO₂Me 4-296 Br O(CH₂)₂OMeSO₂Et 4-297 Br O(CH₂)₃OMe SO₂Me 4-298 Br O(CH₂)₃OMe SO₂Et 4-299 BrO(CH₂)₄OMe SO₂Me 4-300 Br O(CH₂)₄OMe SO₂Et 4-301 Br [1,4]dioxan-2-yl-SO₂Me methoxy 4-302 Br [1,4]dioxan-2-yl- SO₂Et methoxy 4-303 IO(CH₂)₂OMe SO₂Me 4-304 I O(CH₂)₂OMe SO₂Et 4-305 I O(CH₂)₃OMe SO₂Me 4-306I O(CH₂)₃OMe SO₂Et 4-307 I O(CH₂)₄OMe SO₂Me 4-308 I O(CH₂)₄OMe SO₂Et4-309 I [1,4]dioxan-2-yl- SO₂Me methoxy 4-310 I [1,4]dioxan-2-yl- SO₂Etmethoxy 4-311 OMe SMe CF₃ 4-312 OMe SOMe CF₃ 4-313 OMe SO₂Me CF₃ 4-314OMe SOEt CF₃ 4-315 OMe SO₂Et CF₃ 4-316 OMe S(CH₂)₂OMe CF₃ 4-317 OMeSO(CH₂)₂OMe CF₃ 4-318 OMe SO₂(CH₂)₂OMe CF₃ 4-319 OMe SMe Cl 4-320 OMeSOMe Cl 4-321 OMe SO₂Me Cl 4-322 OMe SEt Cl 4-323 OMe SOEt Cl 4-324 OMeSO2Et Cl 4-325 OMe S(CH₂)₂OMe Cl 4-326 OMe SO(CH₂)₂OMe Cl 4-327 OMeSO₂(CH₂)₂OMe Cl 4-328 OCH₂c-Pr SMe CF₃ 4-329 OCH₂c-Pr SOMe CF₃ 4-330OCH₂c-Pr SO₂Me CF₃ 4-331 OCH₂c-Pr SEt CF₃ 4-332 OCH₂c-Pr SOEt CF₃ 4-333OCH₂c-Pr SO₂Et CF₃ 4-334 OCH₂c-Pr S(CH₂)₂OMe CF₃ 4-335 OCH₂c-PrSO(CH₂)₂OMe CF₃ 4-336 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 4-337 OCH₂c-Pr SMe Cl4-338 OCH₂c-Pr SOMe Cl 4-339 OCH₂c-Pr SO₂Me Cl 4-340 OCH₂c-Pr SEt Cl4-341 OCH₂c-Pr SOEt Cl 4-342 OCH₂c-Pr SO₂Et Cl 4-343 OCH₂c-Pr S(CH₂)₂OMeCl 4-344 OCH₂c-Pr SO(CH₂)₂OMe Cl 4-345 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 4-346OCH₂c-Pr SMe SO₂Me 4-347 OCH₂c-Pr SOMe SO₂Me 4-348 OCH₂c-Pr SO₂Me SO₂Me4-349 OCH₂c-Pr SEt SO₂Me 4-350 OCH₂c-Pr SOEt SO₂Me 4-351 OCH₂c-Pr SO₂EtSO₂Me 4-352 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 4-353 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me4-354 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 4-355 SO₂Me F CF₃ 4-356 SO₂Me NH₂ CF₃4-357 SO₂Me NHEt Cl 4-358 SMe SEt F 4-359 SMe SMe F 4-360 Cl SMe CF₃4-361 Cl S(O)Me CF₃ 4-362 Cl SO₂Me CF₃ 4-363 Cl SO₂Me SO₂Me

TABLE 5 Inventive compounds of the general formula (I) in which A is CYand R is CH₂OMe

Physical data No. X Y Z (¹H NMR, DMSO-d₆, 400 MHz) 5-1 F H Cl 5-2 F HSO₂Me 5-3 F H SO₂Et 5-4 F H CF₃ 5-5 F H NO₂ 5-6 Cl H Br 5-7 Cl H SMe 5-8Cl H SOMe 5-9 Cl H SO₂Me 5-10 Cl H SO₂CH₂Cl 5-11 Cl H SEt 5-12 Cl HSO₂Et 5-13 Cl H CF₃ 5-14 Cl H NO₂ 5-15 Cl H pyrazol-1-yl 5-16 Cl H1H-1,2,4-triazol-1-yl 5-17 Br H Cl 5-18 Br H Br 5-19 Br H SO₂Me 5-20 BrH SO₂Et 5-21 Br H CF₃ 5-22 SO₂Me H Cl 5-23 SO₂Me H Br 5-24 SO₂Me H SMe5-25 SO₂Me H SOMe 5-26 SO₂Me H SO₂Me 5-27 SO₂Me H SO₂Et 5-28 SO₂Me H CF₃¹H NMR, CDCl₃, 400 MHz 8.02 (t, 1H), 7.97 (d, 1H), 7.88 (d, 1H), 4.57(s, 2H), 3.43 (s, 3H) 5-29 SO₂Et H Cl 5-30 SO₂Et H Br 5-31 SO₂Et H SMe5-32 SO₂Et H SOMe 5-33 SO₂Et H SO₂Me 5-34 SO₂Et H CF₃ 5-35 NO₂ H F 5-36NO₂ H Cl 5-37 NO₂ H Br ¹H NMR, DMSO-d₆, 400 MHz 8.39 (d, 1H), 8.09 (d,1H), 7.80 (m, 1H), 4.60 (s, 2H), 3.34 (s, 3H) 5-38 NO₂ H I 5-39 NO₂ H CN5-40 NO₂ H SO₂Me 5-41 NO₂ H SO₂Et 5-42 NO₂ H CF₃ 5-43 Me H Cl 5-44 Me HBr 5-45 Me H SMe 5-46 Me H SO₂Me 5-47 Me H SO₂CH₂Cl 5-48 Me H SEt 5-49Me H SO₂Et 5-50 Me H CF₃ 5-51 CH₂SO₂Me H CF₃ ¹H NMR, DMSO-d₆, 400 MHz12.50 (bs, 1H), 7.95 (m, 3H), 4.93 (s, 2H), 4.11 (s, 2H), 3.36 (s, 3H),2.98 (s, 3H) 5-52 Et H Cl 5-53 Et H Br 5-54 Et H SMe 5-55 Et H SO₂Me5-56 Et H SO₂CH₂Cl 5-57 Et H SEt 5-58 Et H SO₂Et 5-59 Et H CF₃ 5-60 CF₃H Cl 5-61 CF₃ H Br 5-62 CF₃ H SO₂Me 5-63 CF₃ H SO₂Et 5-64 CF₃ H CF₃ 5-65NO₂ NH₂ F 5-66 NO₂ NHMe F 5-67 NO₂ NMe₂ F 5-68 NO₂ Me Cl 5-69 NO₂ NH₂ Cl5-70 NO₂ NHMe Cl 5-71 NO₂ NMe₂ Cl 5-72 NO₂ NH₂ Br 5-73 NO₂ NHMe Br 5-74NO₂ NMe₂ Br 5-75 NO₂ NH₂ CF₃ 5-76 NO₂ NMe₂ CF₃ 5-77 NO₂ NH₂ SO₂Me 5-78NO₂ NH₂ SO₂Et 5-79 NO₂ NHMe SO₂Me 5-80 NO₂ NMe₂ SO₂Me 5-81 NO₂ NMe₂SO₂Et 5-82 NO₂ NH₂ 1H-1,2,4-triazol-1-yl 5-83 NO₂ NHMe1H-1,2,4-triazol-1-yl 5-84 NO₂ NMe₂ 1H-1,2,4-triazol-1-yl 5-85 Me SMe H5-86 Me SOMe H 5-87 Me SO₂Me H 5-88 Me SEt H 5-89 Me SOEt H 5-90 MeSO₂Et H 5-91 Me S(CH₂)₂OMe H 5-92 Me SO(CH₂)₂OMe H 5-93 Me SO₂(CH₂)₂OMeH 5-94 Me F F 5-95 Me F Cl 5-96 Me SEt F 5-97 Me SOEt F 5-98 Me SO₂Et F5-99 Me Me Cl 5-100 Me F Cl 5-101 Me Cl Cl 5-102 Me NH₂ Cl 5-103 Me NHMeCl 5-104 Me NMe₂ Cl 5-105 Me O(CH₂)₂OMe Cl 5-106 Me O(CH₂)₃OMe Cl 5-107Me O(CH₂)₄OMe Cl 5-108 Me OCH₂CONMe₂ Cl 5-109 Me O(CH₂)₂—CO—NMe₂ Cl5-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 5-111 Me O(CH₂)₂— Cl NH(CO)NHCO₂Et 5-112Me O(CH₂)₂—NHCO₂Me Cl 5-113 Me OCH₂—NHSO₂cPr Cl 5-114 MeO(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 5-115 MeO(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 5-116 Me SMe Cl 5-117 Me SOMe Cl5-118 Me SO₂Me Cl 5-119 Me SEt Cl 5-120 Me SOEt Cl 5-121 Me SO₂Et Cl5-122 Me S(CH₂)₂OMe Cl 5-123 Me SO(CH₂)₂OMe Cl 5-124 Me SO₂(CH₂)₂OMe Cl5-125 Me NH₂ Br 5-126 Me NHMe Br 5-127 Me NMe₂ Br 5-128 Me OCH₂(CO)NMe₂Br 5-129 Me O(CH₂)-5-pyrrolidin-2- Br one 5-130 Me SMe Br 5-131 Me SOMeBr 5-132 Me SO₂Me Br 5-133 Me SEt Br 5-134 Me SOEt Br 5-135 Me SO₂Et Br5-136 Me SMe I 5-137 Me SOMe I 5-138 Me SO₂Me I 5-139 Me SEt I 5-140 MeSOEt I 5-141 Me SO₂Et I 5-142 Me Cl CF₃ 5-143 Me SMe CF₃ 12.33 (s, 1H),7.78 (d, 1H), 7.71 (d, 1H), 4.62 (s, 2H), 3.36 (s, 3H), 2.66 (s, 3H),2.28 (s, 3H) 5-144 Me SOMe CF₃ 5-145 Me SO₂Me CF₃ 7.89 (bs, 2H), 4.51(s, 2H), 3.31 (s, 3H), 2.08 (s, 3H) 5-146 Me SEt CF₃ 5-147 Me SOEt CF₃5-148 Me SO₂Et CF₃ 5-149 Me S(CH₂)₂OMe CF₃ 5-150 Me SO(CH₂)₂OMe CF₃5-151 Me SO₂(CH₂)₂OMe CF₃ 5-152 Me Me SO₂Me 5-153 Me4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 5-154 Me 4,5-dihydro-1,2-oxazol-SO₂Et 3-yl 5-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl5-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-157 Me NH₂SO₂Me 5-158 Me NHMe SO₂Me 5-159 Me NMe₂ SO₂Me 5-160 Me NH(CH₂)₂OMe SO₂Me12.27 (bs, 1H), 7.64 (d, 1H), 7.19 (d, 1H), 5.69 (m, 2H), 4.62 (s, 2H),3.55 (m, 5H), 2.29 (s, 3H) 5-161 Me pyrazol-1-yl SO₂Me 5-162 Me OH SO₂Me5-163 Me OMe SO₂Me 5-164 Me OMe SO₂Et 5-165 Me OEt SO₂Me 5-166 Me OEtSO₂Et 5-167 Me OiPr SO₂Me 5-168 Me OiPr SO₂Et 5-169 Me O(CH₂)₂OMe SO₂Me5-170 Me O(CH₂)₂OMe SO₂Et 5-171 Me O(CH₂)₃OMe SO₂Me 5-172 Me O(CH₂)₃OMeSO₂Et 5-173 Me O(CH₂)₄OMe SO₂Me 5-174 Me O(CH₂)₄OMe SO₂Et 5-175 MeO(CH₂)₂NHSO2Me SO₂Me 5-176 Me O(CH₂)₂NHSO2Me SO₂Et 5-177 Me OCH₂(CO)NMe₂SO₂Me 5-178 Me OCH₂(CO)NMe₂ SO₂Et 5-179 Me [1,4]dioxan-2-yl-methoxySO₂Me 5-180 Me [1,4]dioxan-2-yl-methoxy SO₂Et 5-181 MeO(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2-yl) 5-182 Me Cl SO₂Me 5-183Me SMe SO₂Me 5-184 Me SOMe SO₂Me 5-185 Me SO₂Me SO₂Me 8.24 (d,1H), 8.04(d, 1H), 4.62 (s, 2H), 3.60 (s, 3H), 3.55 (s, 3H), 3.33 (s, 3H), 2.67(s, 3H) 5-186 Me SO₂Me SO₂Et 5-187 Me SEt SO₂Me 5-188 Me SOEt SO₂Me5-189 Me SO₂Et SO₂Me 5-190 Me S(CH₂)₂OMe SO₂Me 5-191 Me SO(CH₂)₂OMeSO₂Me 5-192 Me SO₂(CH₂)₂OMe SO2Me 5-193 CH₂SMe OMe SO₂Me 5-194 CH₂OMeOMe SO₂Me 5-195 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 5-196 CH₂O(CH₂)₂NH(CH₂)₃OEt SO₂Me OMe 5-197 CH₂O(CH₂)₃ OMe SO₂Me OMe 5-198 CH₂O(CH₂)₂NH(CH₂)₂OMe SO₂Me OMe 5-199 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 5-200 EtSMe Cl 5-201 Et SO₂Me Cl 5-202 Et SMe CF₃ 5-203 Et SO₂Me CF₃ 5-204 Et FSO₂Me 5-205 Et NH(CH₂)₂OMe SO₂Me 5-206 iPr SO₂Me CF₃ 5-207 cPr SO₂Me CF₃5-208 CF₃ O(CH₂)₂OMe F 5-209 CF₃ O(CH₂)₃OMe F 5-210 CF₃ OCH₂CONMe₂ F5-211 CF₃ [1,4]dioxan-2-yl-methoxy F 5-212 CF₃ O(CH₂)₂OMe Cl 5-213 CF₃O(CH₂)₃OMe Cl 5-214 CF₃ OCH₂CONMe₂ Cl 5-215 CF₃ [1,4]dioxan-2-yl-methoxyCl 5-216 CF₃ O(CH₂)₂OMe Br 5-217 CF₃ O(CH₂)₃OMe Br 5-218 CF₃ OCH₂CONMe₂Br 5-219 CF₃ [1,4]dioxan-2-yl-methoxy Br 5-220 CF₃ O(CH₂)₂OMe I 5-221CF₃ O(CH₂)₃OMe I 5-222 CF₃ OCH₂CONMe₂ I 5-223 CF₃[1,4]dioxan-2-yl-methoxy I 5-224 CF₃ F SO₂Me 5-225 CF₃ F SO₂Et 5-226 CF₃O(CH₂)₂OMe SO₂Me 5-227 CF₃ O(CH₂)₂OMe SO₂Et 5-228 CF₃ O(CH₂)₃OMe SO₂Me5-229 CF₃ O(CH₂)₃OMe SO₂Et 5-230 CF₃ OCH₂CONMe₂ SO₂Me 5-231 CF₃OCH₂CONMe₂ SO₂Et 5-232 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Me 5-233 CF₃[1,4]dioxan-2-yl-methoxy SO₂Et 5-234 F SMe CF₃ 7.86 (d, 1H), 7.78 (d,1H), 4.63 (s, 2H), 4.18 (s, 3H), 3.40 (s, 3H) 5-235 F SOMe CF₃ 7.87 (d,1H), 7.82 (d, 1H), 4.63 (s, 2H), 3.13 (ss, 6H) 5-236 Cl Me Cl 5-237 ClOCH₂CHCH₂ Cl 5-238 Cl OCH₂CHF₂ Cl 5-239 Cl O(CH₂)₂OMe Cl 5-240 ClOCH₂CONMe₂ Cl 7.65 (d, 1H), 7.48 (d, 1H), 4.70 (s, 2H), 3.43-3.24 (m,5H), 3.0 (s, 3H), 2.86 (s, 3H) 5-241 Cl O(CH₂)-5-pyrrolidin-2- Cl one5-242 Cl SMe Cl 7.72 (d, 1H), 7.63 (d, 1H), 4.61 (s, 2H), 3.35 (s, 3H),2.44 (s, 3H) 5-243 Cl SOMe Cl 5-244 Cl SO₂Me Cl 5-245 Cl F SMe 5-246 ClCl SO₂Me 8.0 (d, 1H), 7.67 (d, 1H), 4.46 (s, 2H), 3.43 (s, 3H), 3.36 (s,3H) 5-247 Cl COOMe SO₂Me 5-248 Cl CONMe₂ SO₂Me 5-249 Cl CONMe(OMe) SO₂Me5-250 Cl CH₂OMe SO₂Me 5-251 Cl CH₂OMe SO₂Et 5-252 Cl CH₂OEt SO₂Me 5-253Cl CH₂OEt SO₂Et 5-254 Cl CH₂OCH₂CHF₂ SO₂Me 5-255 Cl CH₂OCH₂CF₃ SO₂Me5-256 Cl CH₂OCH₂CF₃ SO₂Et 5-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 5-258 ClCH₂OcPentyl SO₂Me 5-259 Cl CH₂PO(OMe)₂ SO₂Me 5-260 Cl4,5-dihydro-1,2-oxazol- SMe 3-yl 5-261 Cl 4,5-dihydro-1,2-oxazol- SO₂Me3-yl 5-262 Cl 4,5-dihydro-1,2-oxazol- SO₂Et 3-yl 5-263 Cl5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 5-264 Cl5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-265 Cl5-(methoxymethyl)-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-266 Cl5-(methoxymethyl)-5- SO₂Et methyl-4,5-dihydro-1,2- oxazol-3-yl 5-267 ClCH₂O-tetrahydrofuran-3- SO₂Me yl 5-268 Cl CH₂O-tetrahydrofuran-3- SO₂Etyl 5-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 5-270 Cl CH₂OCH₂- SO₂Et12.68 (bs, 1H), 8.09 (d, 1H), tetrahydrofuran-2-yl 7.91 (d, 1H), 5.12(d, 2H), 5.06 (s, 2H), 4.62 (s, 2H), 3.97 (m, 1H), 3.72 (q, 1H), 3.62(q, 1H), 3.37 (s, 3H), 1.94-1.85 (m, 1H), 1.83-1.73 (m, 2H), 1.59- 1.48(m, 1H) 5-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 5-272 Cl CH₂OCH₂-SO₂Et tetrahydrofuran-3-yl 5-273 Cl OMe SO₂Me 5-274 Cl OMe SO₂Et 5-275Cl OEt SO₂Me 5-276 Cl OEt SO₂Et 5-277 Cl OiPr SO₂Me 5-278 Cl OiPr SO₂Et5-279 Cl O(CH₂)₂OMe SO₂Me 5-280 Cl O(CH₂)₄OMe SO₂Me 5-281 Cl O(CH₂)₄OMeSO₂Et 5-282 Cl O(CH₂)₃OMe SO₂Me 5-283 Cl O(CH₂)₃OMe SO₂Et 5-284 ClO(CH₂)₂OMe SO₂Me 5-285 Cl O(CH₂)₂OMe SO₂Et 5-286 Cl[1,4]dioxan-2-yl-methoxy SO₂Me 5-287 Cl [1,4]dioxan-2-yl-methoxy SO₂Et5-288 Cl OCH₂(CO)NMe₂ SO₂Me 5-289 Cl OCH₂(CO)NMe₂ SO₂Et 5-290 Cl SMeSO₂Me 8.12 (d, 1H), 7.91 (d, 1H), 4.62 (s, 2H), 3.57 (s, 3H), 3.40 (s,3H) 5-291 Cl SOMe SO₂Me 5-292 Br OMe Br 5-293 Br O(CH₂)₂OMe Br 5-294 BrO(CH₂)₂OMe SO₂Me 5-295 Br O(CH₂)₂OMe SO₂Et 5-296 Br O(CH₂)₃OMe SO₂Me5-297 Br O(CH₂)₃OMe SO₂Et 5-298 Br O(CH₂)₄OMe SO₂Me 5-299 Br O(CH₂)₄OMeSO₂Et 5-300 Br [1,4]dioxan-2-yl-methoxy SO₂Me 5-301 Br[1,4]dioxan-2-yl-methoxy SO₂Et 5-302 I O(CH₂)₂OMe SO₂Me 5-303 IO(CH₂)₂OMe SO₂Et 5-304 I O(CH₂)₃OMe SO₂Me 5-305 I O(CH₂)₃OMe SO₂Et 5-306I O(CH₂)₄OMe SO₂Me 5-307 I O(CH₂)₄OMe SO₂Et 5-308 I[1,4]dioxan-2-yl-methoxy SO₂Me 5-309 I [1,4]dioxan-2-yl-methoxy SO₂Et5-310 OMe SMe CF₃ 5-311 OMe SOMe CF₃ 5-312 OMe SO₂Me CF₃ 5-313 OMe SOEtCF₃ 5-314 OMe SO₂Et CF₃ 5-315 OMe S(CH₂)₂OMe CF₃ 5-316 OMe SO(CH₂)₂OMeCF₃ 5-317 OMe SO₂(CH₂)₂OMe CF₃ 5-318 OMe SMe Cl 5-319 OMe SOMe Cl 5-320OMe SO₂Me Cl 5-321 OMe SEt Cl 5-322 OMe SOEt Cl 5-323 OMe SO2Et Cl 5-324OMe S(CH₂)₂OMe Cl 5-325 OMe SO(CH₂)₂OMe Cl 5-326 OMe SO₂(CH₂)₂OMe Cl5-327 OMe H SO₂Me 7.79 (d, 1H), 7.61 (d, 2H), 4.62 (s, 2H), 3.95 (s, 3H)5-328 OCH₂-c-Pr SMe CF₃ 5-329 OCH₂-c-Pr SOMe CF₃ 5-330 OCH₂-c-Pr SO₂MeCF₃ 5-331 OCH₂-c-Pr SEt CF₃ 5-332 OCH₂-c-Pr SOEt CF₃ 5-333 OCH₂-c-PrSO₂Et CF₃ 5-334 OCH₂-c-Pr S(CH₂)₂OMe CF₃ 5-335 OCH₂-c-Pr SO(CH₂)₂OMe CF₃5-336 OCH₂-c-Pr SO₂(CH₂)₂OMe CF₃ 5-337 OCH₂-c-Pr SMe Cl 5-338 OCH₂-c-PrSOMe Cl 5-339 OCH₂-c-Pr SO₂Me Cl 5-340 OCH₂-c-Pr SEt Cl 5-341 OCH₂-c-PrSOEt Cl 5-342 OCH₂-c-Pr SO₂Et Cl 5-343 OCH₂-c-Pr S(CH₂)₂OMe Cl 5-344OCH₂-c-Pr SO(CH₂)₂OMe Cl 5-345 OCH₂-c-Pr SO₂(CH₂)₂OMe Cl 5-346 OCH₂-c-PrSMe SO₂Me 5-347 OCH₂-c-Pr SOMe SO₂Me 5-348 OCH₂-c-Pr SO₂Me SO₂Me 5-349OCH₂-c-Pr SEt SO₂Me 5-350 OCH₂-c-Pr SOEt SO₂Me 5-351 OCH₂-c-Pr SO₂EtSO₂Me 5-352 OCH₂-c-Pr S(CH₂)₂OMe SO₂Me 5-353 OCH₂-c-Pr SO(CH₂)₂OMe SO₂Me5-354 OCH₂-c-Pr SO₂(CH₂)₂OMe SO₂Me 5-355 SO₂Me F CF₃ 5-356 SO₂Me NH₂ CF₃5-357 SO₂Me NHEt Cl 5-358 SMe SEt F 5-359 SMe SMe F 5-360 F SO₂Me CF₃5-361 Cl SMe CF₃ 12.58 (bs, 1H), 7.94 (d, 1H), 7.87 (d, 1H), 4.63 (s,2H), 2.44 (s, 3H) 5-362 Cl S(O)Me CF₃ 12.70 (bs, 1H), 8.04 (d, 1H), 8.01(d, 1H), 4.63 (s, 2H), 3.57 (s, 3H), 3.15 (s, 3H) 5-363 Cl SO₂Me CF₃12.75 (bs, 1H), 8.19 (d, 1H), 8.17 (d, 1H), 4.63 (s, 2H), 3.52 (s, 3H),3.32 (s, 3H) 5-364 Cl SO₂Me SO₂Me

TABLE 6 Inventive compounds of the general formula (I) in which A is CY

No. R X Y Z Physical data 6-1 c-Pr NO₂ H SO₂Me 6-2 c-Pr Cl H SO₂Me 6-3c-Pr SO₂Me H CF₃ 6-4 c-Pr NO₂ H OMe 6-5 c-Pr NO₂ H Br 6-6 c-Pr NO₂ H Cl6-7 c-Pr NO₂ H CF₃ 6-8 c-Pr NO₂ H NO₂ 6-9 c-Pr NO₂ H Me 6-10 c-Pr NO₂ HF 6-11 c-Pr OMe H SO₂Me 6-12 c-Pr CF₃ H NO₂ 6-13 c-Pr CF₃ H Cl ¹H NMR,DMSO-d₆, 400 MHz 12.32 (bs, 1H), 7.97 (s, 1H), 7.90 (d, 1H), 7.80 (d,1H), 2.19 (m, 1H), 1.09 (m, 2H), 0.96 (m, 2H) 6-14 c-Pr CH₂SO₂Me H Br6-15 c-Pr Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.09 (d, 1H),7.91 (d, 1H), 5.22 (s, 2H), 4.29 (q, 2H), 3.40 (s, 3H), 2.20 (m, 1H),1.15-0.86 (m, 4H) 6-16 c-Pr Cl CH₂OCH₂CF₃ SMe 6-17 c-Pr Cl5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 6-18 c-Pr Cl4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-19 c-Pr Cl CH₂OCH₂- SO₂Me ¹H NMR,DMSO-d₆, 400 MHz tetrahydrofuran- 12.24 (bs, 1H), 8.17 (d, 1H), 8.132-yl (d, 1H), 5.13 (s, 2H), 4.01-3.93 (m, 1H), 3.72 (dd, 1H), 3.64-3.53(m, 3H), 3.40 (s, 2H), 2.0-1.92 (m, 1H), 1.92-1.86 (m, 1H), 1.82- 1.73(m, 2H), 1.58-1.49 (m, 1H), 1.13-1.07 (m, 1H), 0.98-0.88 (m, 4H) 6-20c-Pr Cl SMe Cl 6-21 c-Pr Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.09 (d,1H), 7.88 (d, 1H), 3.57 (s, 3H), 2.20 (m, 1H), 1.11 (m, 2H), 0.97 (m,2H) 6-22 c-Pr Cl Me SO₂Et 6-23 c-Pr Cl O(CH₂)₂OMe Cl 6-24 c-Pr Cl OCH₂-Cl cyclopropyl 6-25 c-Pr Cl OMe Cl 6-26 c-Pr Cl NHAc Cl 6-27 c-Pr ClOCH₂C(O)NMe₂ Cl 6-28 c-Pr Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.48(bs, 1H), 8.12 (d, 1H), 7.88 (d, 1H), 3.49 (s, 3H), 2.21-2.17 (m, 1H),1.14-1.09 (m, 2H), 1.02- 0.92 (m, 2H) 6-29 c-Pr Cl pyrazol-1-yl SO₂Me6-30 c-Pr Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-31 c-Pr Cl1,2,3-triazol-1-yl SO₂Me 6-32 c-Pr Cl 1,2,3-triazol-2-yl SO₂Me 6-33 c-PrCl F SO₂Me 6-34 c-Pr Me SO₂Me SO₂Me 6-35 c-Pr Me SO₂Me CF₃ 6-36 c-Pr MeNMe₂ SO₂Me 6-37 c-Pr Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.23 (bs,1H), 7.83 (2d, 2H), 3.05 (s, 3H), 2.82 (s, 3H), 2.23- 2.15 (m, 1H),1.16-1.07 (m, 2H), 1.0-0.92 (m, 2H) 6-38 c-Pr Me SMe CF₃ ¹H NMR,DMSO-d₆, 400 MHz 11.02 (bs, 1H), 7.79 (d, 1H), 7.74 (d, 1H), 2.67 (s,3H), 2.30 (s, 3H), 1.23-1.09 (m, 2H), 0.98-0.92 (m, 2H) 6-39 c-Pr MeSO₂CH₂CH₂OMe CF₃ 6-40 c-Pr Me pyrazol-1-yl SO₂Me 6-41 c-Pr Me 4-methoxy-SO₂Me pyrazol-1-yl 6-42 c-Pr Me 1,2,3-triazol-1-yl SO₂Me 6-43 c-Pr Me1,2,3-triazol-2-yl SO₂Me 6-44 c-Pr Me Cl SO₂Me 6-45 c-Pr Me Me SO₂Me6-46 c-Pr Me F Cl ¹H NMR, DMSO-d₆, 400 MHz 12.07 (bs, 1H), 7.59 (dd,1H), 7.43 (d, 1H), 2.31 (s, 3H), 2.18 (m, 1H), 1.10 (m, 2H), 0.95 (m,2H) 6-47 c-Pr Me SO₂Me Cl 6-48 c-Pr Me NMe₂ SO₂Me 6-49 c-Pr MeNH(CH₂)₂OMe SO₂Me 6-50 c-Pr CF₃ F SO₂CH₃ 6-51 c-Pr CF₃ SMe SO₂CH₃ 6-52c-Pr CF₃ SEt SO₂CH₃ 6-53 c-Pr CF₃ S(O)Et SO₂CH₃ 6-54 c-Pr CF₃ SO₂CH₃SO₂CH₃ 6-55 c-Pr CF₃ OCH₂CH₂OMe SO₂CH₃ 6-56 c-Pr CF₃ OCH₂(CO)NMe₂ SO₂Me6-57 c-Pr CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl 6-58 c-Pr SMe SMe F 6-59c-Pr SMe SEt F 6-60 c-Pr SO₂CH₃ F Cl 6-61 c-Pr F S(O)Me CF₃ 6-62 c-Pr FSMe CF₃ 6-63 CO₂Et NO₂ H SO₂Me 6-64 CO₂Et Cl H SO₂Me ¹H NMR, CDCl₃, 400MHz 13.03 (s, 1H), 8.14 (d, 1H), 8.02 (dd, 1H), 7.95 (d, 1H), 4.42 (q,2H), 3.38 (s, 3H), 1.34 (t, 3H) 6-65 CO₂Et SO₂Me H CF₃ ¹H NMR, CDCl₃,400 MHz 8.0 (d, 1H), 7.52 (m, 1H), 6.82 (d, 1H), 4.49 (q, 2H), 3.38 (s,3H), 1.44 (t, 3H) 6-66 CO₂Et NO₂ H OMe ¹H NMR, DMSO-d₆, 400 MHz 12.87(bs, 1H), 7.80 (d, 1H), 7.66 (s, 1H), 7.41 (d, 1H), 4.41 (q, 2H), 3.92(s, 3H), 1.32 (t, 3H) 6-67 CO₂Et NO₂ H Br ¹H NMR, DMSO-d₆, 400 MHz 13.03(bs, 1H), 8.44 (s, 1H), 8.14 (d, 1H), 7.79 (d, 1H), 4.40 (q, 2H), 1.32(t, 3H) 6-68 CO₂Et NO₂ H CF₃ 6-69 CO₂Et NO₂ H NO₂ 6-70 CO₂Et NO₂ H Cl ¹HNMR, DMSO-d₆, 400 MHz 13.02 (bs, 1H), 8.33 (s, 1H), 8.03 (d, 1H), 7.88(d, 1H), 4.40 (q, 2H), 1.33 (t, 3H) 6-71 CO₂Et NO₂ H Me ¹H NMR, DMSO-d₆,400 MHz 12.91 (bs, 1H), 8.04 (s, 1H), 7.72 (dd, 2H), 4.41 (q, 2H), 1.33(t, 3H) 6-72 CO₂Et NO₂ H F ¹H NMR, DMSO-d₆, 400 MHz 13.01 (bs, 1H), 8.18(d, 1H), 7.94 (m, 1H), 7.83 (m, 1H), 4.41 (q, 2H), 1.33 (t, 3H) 6-73CO₂Et OMe H SO₂Me 6-74 CO₂Et CF₃ H NO₂ 6-75 CO₂Et CH₂SO₂Me H Br 6-76CO₂Et Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 11.21 (bs, 1H), 8.16(d, 1H), 7.79 (d, 1H), 5.34 (s, 2H), 4.49 (q, 2H), 4.02 (q, 2H), 3.23(s, 3H), 1.43 (t, 3H) 6-77 CO₂Et Cl CH₂OCH₂CF₃ SMe ¹H NMR, DMSO-d₆, 400MHz 12.76 (s, 1H), 7.64 (d, 1H), 7.43 (d, 1H), 4.90 (s, 2H), 4.42 (q,2H), 4.17 (q, 2H), 2.56 (s, 3H), 1.34 (t, 3H) 6-78 CO₂Et Cl5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400 MHz 4,5-dihydro-1,2- 8.13 (d,1H), 7.96 (d, 1H), 5.21- oxazol-3-yl 5.12 (m, 1H), 4.52 (q, 2H), 3.80-3.71 (m, 1H), 3.42-3.24 (m, 3H), 2.98-2.83 (m, 2H), 1.47 (t, 3H), 1.29(t, 3H) 6-79 CO₂Et Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-80 CO₂Et ClCH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-81 CO₂Et Cl SMe Cl 6-82 CO₂Et ClSMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 13.01 (bs, 1H), 8.13 (d, 1H), 7.92(d, 1H), 4.42 (q, 2H), 3.58 (s, 3H), 1.34 (t, 3H) 6-83 CO₂Et Cl Me SO₂Et6-84 CO₂Et Cl O(CH₂)₂OMe Cl 6-85 CO₂Et Cl OCH₂- Cl cyclopropyl 6-86CO₂Et Cl OMe Cl 6-87 CO₂Et Cl NHAc Cl 6-88 CO₂Et Cl OCH₂C(O)NMe₂ Cl 6-89CO₂Et Cl Cl SO₂Me 6-90 CO₂Et Cl pyrazol-1-yl SO₂Me 6-91 CO₂Et Cl4-methoxy- SO₂Me pyrazol-1-yl 6-92 CO₂Et Cl 1,2,3-triazol-1-yl SO₂Me6-93 CO₂Et Cl 1,2,3-triazol-2-yl SO₂Me 6-94 CO₂Et Cl F SO₂Me 6-95 CO₂EtMe SO₂Me SO₂Me 6-96 CO₂Et Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.93(bs, 1H), 7.79 (d, 1H), 7.72 (d, 1H), 4.42 (q, 2H), 2.67 (s, 3H), 2.32(s, 3H), 1.34 (t, 3H) 6-97 CO₂Et Me NMe₂ SO₂Me 6-98 CO₂Et Me S(O)Me CF₃6-99 CO₂Et Me SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.76 (bs, 1H), 8.04 (d,1H), 8.00 (d, 1H), 4.42 (q, 2H), 3.42 (s, 3H), 2.72 (s, 3H), 1.34 (t,3H) 6-100 CO₂Et Me SO₂CH₂CH₂OMe CF₃ 6-101 CO₂Et Me pyrazol-1-yl SO₂Me6-102 CO₂Et Me 4-methoxy- SO₂Me pyrazol-1-yl 6-103 CO₂Et Me1,2,3-triazol-1-yl SO₂Me 6-104 CO₂Et Me 1,2,3-triazol-2-yl SO₂Me 6-105CO₂Et Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.89 (bs, 1H), 8.03 (d, 1H),7.77 (d, 1H), 4.41 (q, 2H), 3.42 (s, 3H), 1.33 (t, 3H) 6-106 CO₂Et Me MeSO₂Me ¹H NMR, DMSO-d₆, 400 MHz 7.78 (d, 1H), 7.44 (d, 1H), 4.35 (q, 2H),3.22 (s, 3H), 2.57 (s, 3H), 2.34 (s, 3H), 1.31 (t, 3H) 6-107 CO₂Et Me MeSMe 6-108 CO₂Et Me SO₂Me Cl 6-109 CO₂Et Me NMe₂ SO₂Me 6-110 CO₂Et MeNH(CH₂)₂OMe SO₂Me 6-111 CO₂Et CF₃ F SO₂CH₃ ¹H NMR, DMSO-d₆, 400 MHz13.22 (bs, 1H), 8.30 (dd, 1H), 7.86 (d, 1H), 4.41 (q, 2H), 3.84 (m, 2H),3.41 (s, 3H), 3.49 (s, 3H), 1.34 (t, 3H) 6-112 CO₂Et CF₃ SMe SO₂CH₃6-113 CO₂Et CF₃ SEt SO₂CH₃ 6-114 CO₂Et CF₃ S(O)Et SO₂CH₃ 6-115 CO₂Et CF₃SO₂CH₃ SO₂CH₃ 6-116 CO₂Et CF₃ OCH₂CH₂OMe SO₂CH₃ 6-117 CO₂Et CF₃OCH₂(CO)NMe₂ SO₂Me 6-118 CO₂Et CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl6-119 CO₂Et SMe SMe F 6-120 CO₂Et SMe SEt F 6-121 CO₂Et SO₂CH₃ F Cl ¹HNMR, DMSO-d₆, 400 MHz 12.92 (bs, 1H), 8.12 (dd, 1H), 7.58 (d, 1H), 4.41(q, 2H), 3.44 (s, 3H), 1.33 (t, 3H) 6-122 CO₂Et F S(O)Me CF₃ 6-123 CO₂EtF SMe CF₃ 6-124 CO₂Me NO₂ H SO₂Me 6-125 CO₂Me Cl H SO₂Me 6-126 CO₂MeSO₂Me H CF₃ 6-127 CO₂Me NO₂ H OMe 6-128 CO₂Me NO₂ H Br 6-129 CO₂Me NO₂ HCF₃ 6-130 CO₂Me NO₂ H NO₂ 6-131 CO₂Me NO₂ H Cl 6-132 CO₂Me NO₂ H Me6-133 CO₂Me NO₂ H F 6-134 CO₂Me OMe H SO₂Me 6-135 CO₂Me CF₃ H NO₂ 6-136CO₂Me CH₂SO₂Me H Br 6-137 CO₂Me Cl CH₂OCH₂CF₃ SO₂Me 6-138 CO₂Me ClCH₂OCH₂CF₃ SMe 6-139 CO₂Me Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-140 CO₂Me Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-141CO₂Me Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-142 CO₂Me Cl SMe Cl6-143 CO₂Me Cl SMe SO₂Me 6-144 CO₂Me Cl Me SO₂Et 6-145 CO₂Me ClO(CH₂)₂OMe Cl 6-146 CO₂Me Cl OCH₂- Cl cyclopropyl 6-147 CO₂Me Cl OMe Cl6-148 CO₂Me Cl NHAc Cl 6-149 CO₂Me Cl OCH₂C(O)NMe₂ Cl 6-150 CO₂Me Cl ClSO₂Me 6-151 CO₂Me Cl pyrazol-1-yl SO₂Me 6-152 CO₂Me Cl 4-methoxy- SO₂Mepyrazol-1-yl 6-153 CO₂Me Cl 1,2,3-triazol-1-yl SO₂Me 6-154 CO₂Me Cl1,2,3-triazol-2-yl SO₂Me 6-155 CO₂Me Cl F SO₂Me 6-156 CO₂Me Me SO₂MeSO₂Me 6-157 CO₂Me Me SO₂Me CF₃ 6-158 CO₂Me Me NMe₂ SO₂Me 6-159 CO₂Me MeS(O)Me CF₃ 6-160 CO₂Me Me SMe CF₃ 6-161 CO₂Me Me SO₂CH₂CH₂OMe CF₃ 6-162CO₂Me Me pyrazol-1-yl SO₂Me 6-163 CO₂Me Me 4-methoxy- SO₂Me pyrazol-1-yl6-164 CO₂Me Me 1,2,3-triazol-1-yl SO₂Me 6-165 CO₂Me Me1,2,3-triazol-2-yl SO₂Me 6-166 CO₂Me Me Cl SO₂Me 6-167 CO₂Me Me Me SO₂Me6-168 CO₂Me Me Me SMe 6-169 CO₂Me Me SO₂Me Cl 6-170 CO₂Me Me NMe₂ SO₂Me6-171 CO₂Me Me NH(CH₂)₂OMe SO₂Me 6-172 CO₂Me CF₃ F SO₂CH₃ 6-173 CO₂MeCF₃ SMe SO₂CH₃ 6-174 CO₂Me CF₃ SEt SO₂CH₃ 6-175 CO₂Me CF₃ S(O)Et SO₂CH₃6-176 CO₂Me CF₃ SO₂CH₃ SO₂CH₃ 6-177 CO₂Me CF₃ OCH₂CH₂OMe SO₂CH₃ 6-178CO₂Me CF₃ OCH₂(CO)NMe₂ SO2Me 6-179 CO₂Me CF₃ CH₂O- SO₂Ettetrahydrofuran- 2-yl 6-180 CO₂Me SMe SMe F 6-181 CO₂Me SMe SEt F 6-182CO₂Me SO₂CH₃ F Cl 6-183 CO₂Me F S(O)Me CF₃ 6-184 CO₂Me F SMe CF₃ 6-185benzyl NO₂ H SO₂Me 6-186 benzyl Cl H SO₂Me 6-187 benzyl SO₂Me H CF₃6-188 benzyl NO₂ H OMe 6-189 benzyl NO₂ H Br ¹H NMR, CDCl₃, 400 MHz 7.93(s, 1H), 7.72 (m, 2H), 7.41- 7.28 (m, 5H), 4.09 (s, 2H) 6-190 benzyl NO₂H CF₃ 6-191 benzyl NO₂ H NO₂ 6-192 benzyl NO₂ H Cl ¹H NMR, CDCl₃, 400MHz 7.85-8.73 (m, 2H), 7.59 (dd, 1H), 7.39-7.23 (m, 5H), 4.09 (s, 2H)6-193 benzyl NO₂ H Me 6-194 benzyl NO₂ H F 6-195 benzyl OMe H SO₂Me6-196 benzyl CF₃ H NO₂ 6-197 benzyl CH₂SO₂Me H Br ¹H NMR, DMSO-d₆, 400MHz 7.83-7.72 (m, 2H), 7.68 (m, 1H), 7.40-7.37 (m, 5H), 4.83 (s, 2H),4.28 (s, 2H), 2.91 (s, 3H) 6-198 benzyl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR,DMSO-d₆, 400 MHz 12.49 (s, 1H), 8.08 (d, 1H), 7.92 (d, 1H), 7.39-7.24(m, 5H), 5.23 (s, 2H), 4.27 (q, 2H), 3.39 (s, 3H) 6-199 benzyl ClCH₂OCH₂CF₃ SMe ¹H NMR, DMSO-d₆, 400 MHz 12.18 (s, 1H), 7.59 (d, 1H),7.40- 7.28 (m, 6H), 4.89 (s, 2H), 4.25 (s, 2H), 4.16 (q, 2H), 2.56 (s,3H) 6-200 benzyl Cl 5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400 MHz4,5-dihydro-1,2- 8.04 (d, 1H), 7.98 (d, 1H), 7.41- oxazol-3-yl 7.24 (m,5H), 5.19-5.09 (m, 1H), 3.78-3.69 (m, 1H), 3.36 (q, 2H), 3.28-3.18 (m,1H), 2.98-2.78 (m, 2H), 1.28 (m, 5H) 6-201 benzyl Cl 4,5-dihydro-1,2-SO₂Et oxazol-3-yl 6-202 benzyl Cl CH₂OCH₂- SO₂Me ¹H NMR, CDCl₃, 400 MHztetrahydrofuran- 8.09 (d, 1H), 7.72 (d, 1H), 7.40- 2-yl 7.29 (m, 5H),5.27 (s, 2H), 4.13 (s, 2H), 4.10-4.02 (m, 1H), 3.79 (q, 1H), 3.71 (q,1H), 3.68-3.57 (m, 2H), 3.28 (s, 3H), 2.01-1.90 (m, 1H), 1.90-1.81 (m,2H), 1.62- 1.51 (m, 1H) 6-203 benzyl Cl SMe Cl 6-204 benzyl Cl SMe SO₂Me6-205 benzyl Cl Me SO₂Et 6-206 benzyl Cl O(CH₂)₂OMe Cl 6-207 benzyl ClOCH₂- Cl cyclopropyl 6-208 benzyl Cl OMe Cl 6-209 benzyl Cl NHAc Cl6-210 benzyl Cl OCH₂C(O)NMe₂ Cl 6-211 benzyl Cl Cl SO₂Me 6-212 benzyl Clpyrazol-1-yl SO₂Me 6-213 benzyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-214benzyl Cl 1,2,3-triazol-1-yl SO₂Me 6-215 benzyl Cl 1,2,3-triazol-2-ylSO₂Me 6-216 benzyl Cl F SO₂Me 6-217 benzyl Me SO₂Me SO₂Me 6-218 benzylMe SO₂Me CF₃ 6-219 benzyl Me NMe₂ SO₂Me 6-220 benzyl Me S(O)Me CF₃ 6-221benzyl Me SMe CF₃ 6-222 benzyl Me SO₂CH₂CH₂OMe CF₃ 6-223 benzyl Mepyrazol-1-yl SO₂Me 6-224 benzyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-225benzyl Me 1,2,3-triazol-1-yl SO₂Me 6-226 benzyl Me 1,2,3-triazol-2-ylSO₂Me 6-227 benzyl Me Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.40 (s, 1H),7.99 (d, 1H), 7.72 (d, 1H), 7.40-7.26 (m, 5H), 4.25 (s, 2H), 3.41 (q,2H), 2.42 (s, 3H) 6-228 benzyl Me Me SO₂Me 6-229 benzyl Me Me SMe 6-230benzyl Me SO₂Me Cl 6-231 benzyl Me NMe₂ SO₂Me 6-232 benzyl MeNH(CH₂)₂OMe SO₂Me 6-233 benzyl CF₃ F SO₂CH₃ 6-234 benzyl CF₃ SMe SO₂CH₃6-235 benzyl CF₃ SEt SO₂CH₃ 6-236 benzyl CF₃ S(O)Et SO₂CH₃ 6-237 benzylCF₃ SO₂CH₃ SO₂CH₃ 6-238 benzyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-239 benzyl CF₃OCH₂(CO)NMe₂ SO2Me 6-240 benzyl CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl6-241 benzyl SMe SMe F ¹H NMR, CDCl₃, 400 MHz 10.65 (bs, 1H), 7.73 (m,1H), 7.38-7.28 (m, 5H), 7.16 (t, 1H), 4.18 (s, 2H), 2.53 (s, 3H), 2.44(s, 3H) 6-242 benzyl SMe SEt F ¹H NMR, CDCl₃, 400 MHz 7.49-7.38 (m, 6H),7.24 (t, 1H), 4.19 (s, 2H), 2.92 (q, 2H), 1.23 (t, 3H) 6-243 benzylSO₂CH₃ F Cl 6-244 benzyl F S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 8.18 (t,1H), 8.0 (t, 1H), 7.65 (t, 2H), 7.39-7.21 (m, 3H), 4.17 (s, 2H), 3.11(s, 3H) 6-245 benzyl F SMe CF₃ 6-246 phenyl NO₂ H SO₂Me ¹H NMR, CDCl₃,400 MHz 9.02 (s, 1H), 8.72 (s, 1H), 8.20 (d, 1H), 7.90 (d, 1H),7.29-7.18 (m, 5H) 6-247 phenyl Cl H SO₂Me 6-248 phenyl SO₂Me H CF₃ ¹HNMR, CDCl₃, 400 MHz 8.39 (s, 1H), 8.02-7.90 (m, 4H), 7.61-7.48 (m, 3H),3.47 (s, 3H) 6-249 phenyl NO₂ H OMe 6-250 phenyl NO₂ H Br 6-251 phenylNO₂ H CF₃ 6-252 phenyl NO₂ H NO₂ 6-253 phenyl NO₂ H Cl 6-254 phenyl NO₂H Me 6-255 phenyl NO₂ H F 6-256 phenyl OMe H SO₂Me 6-257 phenyl CF₃ HNO₂ 6-258 phenyl CH₂SO₂Me H Br 6-259 phenyl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR,CDCl₃, 400 MHz 8.19 (d, 1H), 8.01 (d, 2H), 7.91 (d, 1H), 7.65-7.50 (m,3H), 5.39 (s, 2H), 4.04 (q, 2H), 3.22 (s, 3H) 6-260 phenyl Cl CH₂OCH₂CF₃SMe 6-261 phenyl Cl 5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400 MHz4,5-dihydro-1,2- 8.24 (d, 1H), 8.04-7.97 (m, 3H), oxazol-3-yl 7.66-7.51(m, 3H), 5.21-5.09 (m, 1H), 3.81-3.58 (m, 1H), 3.38 (q, 2H), 3.31-3.19(m, 1H), 2.99-2.78 (m, 2H), 1.28 (t, 3H) 6-262 phenyl Cl4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-263 phenyl Cl CH₂OCH₂- SO₂Metetrahydrofuran- 2-yl 6-264 phenyl Cl SMe Cl 6-265 phenyl Cl SMe SO₂Me6-266 phenyl Cl Me SO₂Et 6-267 phenyl Cl O(CH₂)₂OMe Cl 6-268 phenyl ClOCH₂- Cl cyclopropyl 6-269 phenyl Cl OMe Cl 6-270 phenyl Cl NHAc Cl6-271 phenyl Cl OCH₂C(O)NMe₂ Cl 6-272 phenyl Cl Cl SO₂Me 6-273 phenyl Clpyrazol-1-yl SO₂Me 6-274 phenyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-275phenyl Cl 1,2,3-triazol-1-yl SO₂Me 6-276 phenyl Cl 1,2,3-triazol-2-ylSO₂Me 6-277 phenyl Cl F SO₂Me 6-278 phenyl Me SO₂Me SO₂Me 6-279 phenylMe SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.64 (s, 1H), 8.05 (2d, 2H), 7.94(bs, 2H), 7.64-7.61 (m, 3H), 3.49 (s, 3H), 2.76 (s, 3H) 6-280 phenyl MeNMe₂ SO₂Me 6-281 phenyl Me S(O)Me CF₃ 6-282 phenyl Me SMe CF₃ ¹H NMR,DMSO-d₆, 400 MHz 12.46 (s, 1H), 7.93 (d, 2H), 7.80 (d, 1H), 7.75 (d,1H), 7.58-7.64 (m, 3H), 2.69 (s, 3H), 2.32 (s, 3H) 6-283 phenyl MeSO₂CH₂CH₂OMe CF₃ 6-284 phenyl Me pyrazol-1-yl SO₂Me 6-285 phenyl Me4-methoxy- SO₂Me pyrazol-1-yl 6-286 phenyl Me 1,2,3-triazol-1-yl SO₂Me6-287 phenyl Me 1,2,3-triazol-2-yl SO₂Me 6-288 phenyl Me Cl SO₂Me 6-289phenyl Me Me SO₂Me 6-290 phenyl Me Me SMe 6-291 phenyl Me SO₂Me Cl 6-292phenyl Me NMe₂ SO₂Me 6-293 phenyl Me NH(CH₂)₂OMe SO₂Me 6-294 phenyl CF₃F SO₂CH₃ 6-295 phenyl CF₃ SMe SO₂CH₃ 6-296 phenyl CF₃ SEt SO₂CH₃ 6-297phenyl CF₃ S(O)Et SO₂CH₃ 6-298 phenyl CF₃ SO₂CH₃ SO₂CH₃ 6-299 phenyl CF₃OCH₂CH₂OMe SO₂CH₃ 6-300 phenyl CF₃ OCH₂(CO)NMe₂ SO₂Me 6-301 phenyl CF₃CH₂O- SO₂Et tetrahydrofuran- 2-yl 6-302 phenyl SMe SMe F 6-303 phenylSMe SEt F 6-304 phenyl SO₂CH₃ F Cl 6-305 phenyl F S(O)Me CF₃ 6-306phenyl F SMe CF₃ 6-307 pyrazin- NO₂ H SO₂Me 2-yl 6-308 pyrazin- Cl HSO₂Me 2-yl 6-309 pyrazin- SO₂Me H CF₃ ¹H NMR, CDCl₃, 400 MHz 2-yl 9.32(s, 1H), 8.72 (dd, 2H), 8.38 (s, 1H), 8.00 (d, 1H), 7.90 (d, 1H), 3.40(s, 3H) 6-310 pyrazin- NO₂ H OMe 2-yl 6-311 pyrazin- NO₂ H Br 2-yl 6-312pyrazin- NO₂ H CF₃ 2-yl 6-313 pyrazin- NO₂ H NO₂ 2-yl 6-314 pyrazin- NO₂H Cl 2-yl 6-315 pyrazin- NO₂ H Me 2-yl 6-316 pyrazin- NO₂ H F 2-yl 6-317pyrazin- OMe H SO₂Me 2-yl 6-318 pyrazin- CF₃ H NO₂ 2-yl 6-319 pyrazin-CH₂SO₂Me H Br 2-yl 6-320 pyrazin- Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400MHz 2-yl 9.39 (s, 1H), 8.78 (dd, 2H), 8.23 (d, 1H), 7.90 (d, 1H), 5.39(m, 2H), 4.05 (q, 2H), 3.23 (s, 3H) 6-321 pyrazin- Cl CH₂OCH₂CF₃ SMe2-yl 6-322 pyrazin- Cl 5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400 MHz 2-yl4,5-dihydro-1,2- 9.38 (s, 1H), 8.78 (d, 2H), 8.13 oxazol-3-yl (d, 1H),8.04 (d, 1H), 5.12-5.11 (m, 1H), 3.82-3.71 (m, 1H), 3.39 (q, 2H),3.33-3.24 (dd, 1H), 3.0- 2.81 (m, 1H), 1.3 (t, 3H) 6-323 pyrazin- Cl4,5-dihydro-1,2- SO₂Et 2-yl oxazol-3-yl 6-324 pyrazin- Cl CH₂OCH₂- SO₂Me2-yl tetrahydrofuran- 2-yl 6-325 pyrazin- Cl SMe Cl 2-yl 6-326 pyrazin-Cl SMe SO₂Me 2-yl 6-327 pyrazin- Cl Me SO₂Et 2-yl 6-328 pyrazin- ClO(CH₂)₂OMe Cl 2-yl 6-329 pyrazin- Cl OCH₂- Cl 2-yl cyclopropyl 6-330pyrazin- Cl OMe Cl 2-yl 6-331 pyrazin- Cl NHAc Cl 2-yl 6-332 pyrazin- ClOCH₂C(O)NMe₂ Cl 2-yl 6-333 pyrazin- Cl Cl SO₂Me 2-yl 6-334 pyrazin- Clpyrazol-1-yl SO₂Me 2-yl 6-335 pyrazin- Cl 4-methoxy- SO₂Me 2-ylpyrazol-1-yl 6-336 pyrazin- Cl 1,2,3-triazol-1-yl SO₂Me 2-yl 6-337pyrazin- Cl 1,2,3-triazol-2-yl SO₂Me 2-yl 6-338 pyrazin- Cl F SO₂Me 2-yl6-339 pyrazin- Me SO₂Me SO₂Me 2-yl 6-340 pyrazin- Me SO₂Me CF₃ ¹H NMR,DMSO-d₆, 400 MHz 2-yl 12.84 (s, 1H), 9.33 (s, 1H), 8.86 (2d, 2H), 8.04(2d, 2H), 3.45 (s, 3H), 2.75 (s, 3H) 6-341 pyrazin- Me NMe₂ SO₂Me 2-yl6-342 pyrazin- Me S(O)Me CF₃ 2-yl 6-343 pyrazin- Me SMe CF₃ 2-yl 6-344pyrazin- Me SO₂CH₂CH₂OMe CF₃ 2-yl 6-345 pyrazin- Me pyrazol-1-yl SO₂Me2-yl 6-346 pyrazin- Me 4-methoxy- SO₂Me 2-yl pyrazol-1-yl 6-347 pyrazin-Me 1,2,3-triazol-1-yl SO₂Me 2-yl 6-348 pyrazin- Me 1,2,3-triazol-2-ylSO₂Me 2-yl 6-349 pyrazin- Me Cl SO₂Me 2-yl 6-350 pyrazin- Me Me SO₂Me2-yl 6-351 pyrazin- Me Me SMe 2-yl 6-352 pyrazin- Me SO₂Me Cl 2-yl 6-353pyrazin- Me NMe₂ SO₂Me 2-yl 6-354 pyrazin- Me NH(CH₂)₂OMe SO₂Me 2-yl6-355 pyrazin- CF₃ F SO₂CH₃ 2-yl 6-356 pyrazin- CF₃ SMe SO₂CH₃ 2-yl6-357 pyrazin- CF₃ SEt SO₂CH₃ 2-yl 6-358 pyrazin- CF₃ S(O)Et SO₂CH₃ 2-yl6-359 pyrazin- CF₃ SO₂CH₃ SO₂CH₃ 2-yl 6-360 pyrazin- CF₃ OCH₂CH₂OMeSO₂CH₃ 2-yl 6-361 pyrazin- CF₃ OCH₂(CO)NMe₂ SO2Me 2-yl 6-362 pyrazin-CF₃ CH₂O- SO₂Et 2-yl tetrahydrofuran- 2-yl 6-363 pyrazin- SMe SMe F 2-yl6-364 pyrazin- SMe SEt F 2-yl 6-365 pyrazin- SO₂CH₃ F Cl 2-yl 6-366pyrazin- F S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 2-yl 9.35 (s, 1H), 8.88(s, 2H), 7.90 (d, 1H), 7.83 (d, 1H), 3.17 (s, 3H), 3.12 (s, 3H) 6-367pyrazin- F SMe CF₃ 2-yl 6-368 4-OMe—Ph NO₂ H SO₂Me 6-369 4-OMe—Ph Cl HSO₂Me ¹H NMR, CDCl₃, 400 MHz 12.67 (s, 1H), 8.14 (s, 1H), 8.04 (d, 1H),7.97 (d, 1H), 7.87 (d, 2H), 7.15 (d, 2H), 3.85 (s, 3H), 3.36 (s, 3H)6-370 4-OMe—Ph SO₂Me H CF₃ 6-371 4-OMe—Ph NO₂ H OMe 6-372 4-OMe—Ph NO₂ HBr 6-373 4-OMe—Ph NO₂ H CF₃ 6-374 4-OMe—Ph NO₂ H NO₂ 6-375 4-OMe—Ph NO₂H Cl 6-376 4-OMe—Ph NO₂ H Me 6-377 4-OMe—Ph NO₂ H F 6-378 4-OMe—Ph OMe HSO₂Me 6-379 4-OMe—Ph CF₃ H NO₂ 6-380 4-OMe—Ph CH₂SO₂Me H Br 6-3814-OMe—Ph Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.43 (bs, 1H), 8.02(d, 1H), 7.66 (d, 1H), 7.49 (d, 2H), 6.80 (d, 2H), 5.61 (bs, 1H),5.40-5.27 (m, 2H), 4.03 (q, 2H), 3.05 (s, 3H) 6-382 4-OMe—Ph ClCH₂OCH₂CF₃ SMe 6-383 4-OMe—Ph Cl 5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400MHz 4,5-dihydro-1,2- 8.08 (2d, 2H), 7.92 (d, 2H), 7.03 oxazol-3-yl (d,2H), 5.22-5.12 (m, 1H), 3.83- 3.62 (m, 1H), 3.37 (q, 2H), 3.29- 3.21 (m,1H), 3.0-2.91 (dd, 1H), 2.88-2.79 (dd, 1H), 1.27 (t, 3H) 6-384 4-OMe—PhCl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-385 4-OMe—Ph Cl CH₂OCH₂- SO₂Metetrahydrofuran- 2-yl 6-386 4-OMe—Ph Cl SMe Cl 6-387 4-OMe—Ph Cl SMeSO₂Me 6-388 4-OMe—Ph Cl Me SO₂Et 6-389 4-OMe—Ph Cl O(CH₂)₂OMe Cl 6-3904-OMe—Ph Cl OCH₂- Cl cyclopropyl 6-391 4-OMe—Ph Cl OMe Cl 6-392 4-OMe—PhCl NHAc Cl 6-393 4-OMe—Ph Cl OCH₂C(O)NMe₂ Cl 6-394 4-OMe—Ph Cl Cl SO₂Me6-395 4-OMe—Ph Cl pyrazol-1-yl SO₂Me 6-396 4-OMe—Ph Cl 4-methoxy- SO₂Mepyrazol-1-yl 6-397 4-OMe—Ph Cl 1,2,3-triazol-1-yl SO₂Me 6-398 4-OMe—PhCl 1,2,3-triazol-2-yl SO₂Me 6-399 4-OMe—Ph Cl F SO₂Me 6-400 4-OMe—Ph MeSO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.54 (s, 1H), 8.02 (2d, 2H), 7.89(d, 2H), 7.15 (d, 2H), 3.86 (s, 3H), 3.42 (s, 3H), 2.75 (s, 3H) 6-4014-OMe—Ph Me SO₂Me CF₃ 6-402 4-OMe—Ph Me NMe₂ SO₂Me 6-403 4-OMe—Ph MeS(O)Me CF₃ 6-404 4-OMe—Ph Me SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.37 (s,1H), 7.87 (d, 2H), 7.79 (d, 1H), 7.74 (d, 1H), 7.15 (d, 2H), 3.86 (s,3H), 2.67 (s, 3H), 2.32 (s, 3H) 6-405 4-OMe—Ph Me SO₂CH₂CH₂OMe CF₃ 6-4064-OMe—Ph Me pyrazol-1-yl SO₂Me 6-407 4-OMe—Ph Me 4-methoxy- SO₂Mepyrazol-1-yl 6-408 4-OMe—Ph Me 1,2,3-triazol-1-yl SO₂Me 6-409 4-OMe—PhMe 1,2,3-triazol-2-yl SO₂Me 6-410 4-OMe—Ph Me Cl SO₂Me 6-411 4-OMe—Ph MeMe SO₂Me 6-412 4-OMe—Ph Me Me SMe 6-413 4-OMe—Ph Me SO₂Me Cl 6-4144-OMe—Ph Me NMe₂ SO₂Me 6-415 4-OMe—Ph Me NH(CH₂)₂OMe SO₂Me 6-4164-OMe—Ph CF₃ F SO₂CH₃ 6-417 4-OMe—Ph CF₃ SMe SO₂CH₃ 6-418 4-OMe—Ph CF₃SEt SO₂CH₃ 6-419 4-OMe—Ph CF₃ S(O)Et SO₂CH₃ 6-420 4-OMe—Ph CF₃ SO₂CH₃SO₂CH₃ 6-421 4-OMe—Ph CF₃ OCH₂CH₂OMe SO₂CH₃ 6-422 4-OMe—Ph CF₃OCH₂(CO)NMe₂ SO₂Me 6-423 4-OMe—Ph CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl6-424 4-OMe—Ph SMe SMe F 6-425 4-OMe—Ph SMe SEt F 6-426 4-OMe—Ph SO₂CH₃F Cl 6-427 4-OMe—Ph F S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 8.14 (d, 1H),7.89 (d, 3H), 7.17 (d, 2H), 3.87 (s, 3H), 3.14 (s, 3H) 6-428 4-OMe—Ph FSMe CF₃ 6-429 4-Cl—Ph NO₂ H SO₂Me ¹H NMR, CDCl₃, 400 MHz 8.23 (m, 1H),8.12 (m, 1H), 7.92 (d, 2H), 7.53 (d, 2H), 3.13 (s, 3H) 6-430 4-Cl—Ph ClH SO₂Me 6-431 4-Cl—Ph SO₂Me H CF₃ ¹H NMR, CDCl₃, 400 MHz 8.39 (s, 1H),7.99 (d, 1H), 7.43- 7.34 (m, 3H), 7.49 (d, 2H), 3.43 (s, 3H) 6-4324-Cl—Ph NO₂ H OMe 6-433 4-Cl—Ph NO₂ H Br 6-434 4-Cl—Ph NO₂ H CF₃ 6-4354-Cl—Ph NO₂ H NO₂ 6-436 4-Cl—Ph NO₂ H Cl 6-437 4-Cl—Ph NO₂ H Me 6-4384-Cl—Ph NO₂ H F 6-439 4-Cl—Ph OMe H SO₂Me 6-440 4-Cl—Ph CF₃ H NO₂ 6-4414-Cl—Ph CH₂SO₂Me H Br 6-442 4-Cl—Ph Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, CDCl₃,400 MHz 8.27-8.08 (m, 2H), 7.99-7.81 (m, 2H), 7.57-7.43 (m, 2H),5.48-5.29 (m, 2H), 4.12-3.98 (m, 2H), 3.22 (m, 3H) 6-443 4-Cl—Ph ClCH₂OCH₂CF₃ SMe 6-444 4-Cl—Ph Cl 5-cyanomethyl- SO₂Et ¹H NMR, CDCl₃, 400MHz 4,5-dihydro-1,2- 8.16 (d, 1H), 8.01 (d, 1H), 7.96 oxazol-3-yl (d,2H), 7.53 (d, 2H), 5.20-5.09 (m, 1H), 3.80-3.69 (m, 1H), 3.39 (q, 2H),3.31-3.19 (dd, 1H), 2.98- 2.77 (m, 2H), 1.29 (t, 3H) 6-445 4-Cl—Ph Cl4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-446 4-Cl—Ph Cl CH₂OCH₂- SO₂Metetrahydrofuran- 2-yl 6-447 4-Cl—Ph Cl SMe Cl 6-448 4-Cl—Ph Cl SMe SO₂Me6-449 4-Cl—Ph Cl Me SO₂Et 6-450 4-Cl—Ph Cl O(CH₂)₂OMe Cl 6-451 4-Cl—PhCl OCH₂- Cl cyclopropyl 6-452 4-Cl—Ph Cl OMe Cl 6-453 4-Cl—Ph Cl NHAc Cl6-454 4-Cl—Ph Cl OCH₂C(O)NMe₂ Cl 6-455 4-Cl—Ph Cl Cl SO₂Me 6-456 4-Cl—PhCl pyrazol-1-yl SO₂Me 6-457 4-Cl—Ph Cl 4-methoxy- SO₂Me pyrazol-1-yl6-458 4-Cl—Ph Cl 1,2,3-triazol-1-yl SO₂Me 6-459 4-Cl—Ph Cl1,2,3-triazol-2-yl SO₂Me 6-460 4-Cl—Ph Cl F SO₂Me 6-461 4-Cl—Ph Me SO₂MeSO₂Me 6-462 4-Cl—Ph Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400 MHz 7.98-7.87 (dd,4H), 7.51 (d, 2H), 3.26 (s, 3H), 2.87 (s, 3H) 6-463 4-Cl—Ph Me NMe₂SO₂Me 6-464 4-Cl—Ph Me S(O)Me CF₃ 6-465 4-Cl—Ph Me SMe CF₃ ¹H NMR,CDCl₃, 400 MHz 12.50 (s, 1H), 7.95 (d, 2H), 7.80 (d, 1H), 7.74 (d, 1H),7.69 (d, 2H), 2.69 (s, 3H), 2.32 (s, 3H) 6-466 4-Cl—Ph Me SO₂CH₂CH₂OMeCF₃ 6-467 4-Cl—Ph Me pyrazol-1-yl SO₂Me 6-468 4-Cl—Ph Me 4-methoxy-SO₂Me pyrazol-1-yl 6-469 4-Cl—Ph Me 1,2,3-triazol-1-yl SO₂Me 6-4704-Cl—Ph Me 1,2,3-triazol-2-yl SO₂Me 6-471 4-Cl—Ph Me Cl SO₂Me ¹H NMR,DMSO-d₆, 400 MHz 12.64 (bs, 1H), 8.04 (d, 1H), 7.97 (d, 2H), 7.80 (d,1H), 7.70 (d, 2H), 3.44 (s, 3H) 6-472 4-Cl—Ph Me Me SO₂Me 6-473 4-Cl—PhMe Me SMe 6-474 4-Cl—Ph Me SO₂Me Cl 6-475 4-Cl—Ph Me NMe₂ SO₂Me 6-4764-Cl—Ph Me NH(CH₂)₂OMe SO₂Me 6-477 4-Cl—Ph CF₃ F SO₂CH₃ 6-478 4-Cl—PhCF₃ SMe SO₂CH₃ 6-479 4-Cl—Ph CF₃ SEt SO₂CH₃ 6-480 4-Cl—Ph CF₃ S(O)EtSO₂CH₃ 6-481 4-Cl—Ph CF₃ SO₂CH₃ SO₂CH₃ 6-482 4-Cl—Ph CF₃ OCH₂CH₂OMeSO₂CH₃ 6-483 4-Cl—Ph CF₃ OCH₂(CO)NMe₂ SO₂Me 6-484 4-Cl—Ph CF₃ CH₂O-SO₂Et tetrahydrofuran- 2-yl 6-485 4-Cl—Ph SMe SMe F 6-486 4-Cl—Ph SMeSEt F 6-487 4-Cl—Ph SO₂CH₃ F Cl 6-488 4-Cl—Ph F S(O)Me CF₃ ¹H NMR,DMSO-d₆, 400 MHz 12.90 (bs, 1H), 8.14 (m, 1H), 7.97 (d, 2H), 7.91 (d,1H), 7.69 (d, 2H), 3.14 (s, 3H) 6-489 4-Cl—Ph F SMe CF₃ 6-490 tert- NO₂H SO₂Me butyl 6-491 tert- Cl H SO₂Me ¹H NMR, DMSO-d₆, 400 MHz butyl12.49 (bs, 1H), 8.12 (s, 1H), 8.0 (d, 1H), 7.94 (d, 1H), 1.34 (s, 9H)6-492 tert- SO₂Me H CF₃ ¹H NMR, DMSO-d₆, 400 MHz butyl 8.28 (m, 1H),8.17 (d, 1H), 7.90 (m, 1H), 1.24 (s, 9H) 6-493 tert- NO₂ H OMe butyl6-494 tert- NO₂ H Br ¹H NMR, CDCl₃, 400 MHz butyl 7.92 (s, 1H), 7.83(dd, 1H), 7.76 (dd, 1H), 1.39 (s, 9H) 6-495 tert- NO₂ H CF₃ ¹H NMR,CDCl₃, 400 MHz butyl 8.11 (s, 1H), 8.02 (d, 1H), 7.89 (d, 1H), 1.41 (s,9H) 6-496 tert- NO₂ H NO₂ ¹H NMR, CDCl₃, 400 MHz butyl 8.68 (s, 1H),8.48 (d, 1H), 8.09 (d, 1H), 1.42 (s, 9H) 6-497 tert- NO₂ H Cl butyl6-498 tert- NO₂ H Me ¹H NMR, CDCl₃, 400 MHz butyl 7.92 (s, 1H), 7.57(2d, 2H), 6.59 (bs, 2H), 2.53 (s, 3H), 1.17 (s, 9H) 6-499 tert- NO₂ H Fbutyl 6-500 tert- OMe H SO₂Me butyl 6-501 tert- CF₃ H NO₂ butyl 6-502tert- CH₂SO₂Me H Br butyl 6-503 tert- Cl CH₂OCH₂CF₃ SO₂Me butyl 6-504tert- Cl CH₂OCH₂CF₃ SMe ¹H NMR, DMSO-d₆, 400 MHz butyl 12.18 (bs, 1H),7.61 (d, 1H), 7.41 (d, 1H), 4.89 (s, 2H), 4.17 (q, 2H), 2.55 (s, 3H),1.33 (bs, 9H) 6-505 tert- Cl 5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400MHz butyl 4,5-dihydro-1,2- 12.51 (bs, 1H), 8.08 (dd, 2H), oxazol-3-yl5.23-5.13 (m, 1H), 3.66-3.55 (m, 1H), 3.41 (q, 2H), 3.19-3.10 (dd, 1H),3.03-2.98 (m, 2H), 1.33 (bs, 9H), 1.14 (t, 3H) 6-506 tert- Cl4,5-dihydro-1,2- SO₂Et butyl oxazol-3-yl 6-507 tert- Cl CH₂OCH₂- SO₂Me¹H NMR, CDCl₃, 400 MHz butyl tetrahydrofuran- 8.12 (d, 1H), 7.30 (d,1H), 5.22 2-yl (s, 2H), 4.14-4.04 (m, 1H), 3.82 (q, 1H), 3.64 (q, 1H),3.69-3.60 (m, 2H), 3.30 (s, 3H), 2.0-1.91 (m, 1H), 1.91-1.79 (m, 2H),1.65- 1.56 (m, 1H), 1.41 (s, 9H) 6-508 tert- Cl SMe Cl butyl 6-509 tert-Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz butyl 12.47 (bs, 1H), 8.10 (d,1H), 7.90 (d, 1H), 3.57 (s, 3H), 1.31 (bs, 9H) 6-510 tert- Cl Me SO₂Etbutyl 6-511 tert- Cl O(CH₂)₂OMe Cl butyl 6-512 tert- Cl OCH₂- Cl butylcyclopropyl 6-513 tert- Cl OMe Cl butyl 6-514 tert- Cl NHAc Cl butyl6-515 tert- Cl OCH₂C(O)NMe₂ Cl butyl 6-516 tert- Cl Cl SO₂Me butyl 6-517tert- Cl pyrazol-1-yl SO₂Me butyl 6-518 tert- Cl 4-methoxy- SO₂Me butylpyrazol-1-yl 6-519 tert- Cl 1,2,3-triazol-1-yl SO₂Me butyl 6-520 tert-Cl 1,2,3-triazol-2-yl SO₂Me butyl 6-521 tert- Cl F SO₂Me butyl 6-522tert- Me SO₂Me SO₂Me butyl 6-523 tert- Me SO₂Me CF₃ ¹H NMR, CDCl₃, 400MHz butyl 7.97-7.85 (m, 2H), 3.25 (s, 3H), 2.87 (s, 3H), 1.42 (s, 9H)6-524 tert- Me NMe₂ SO₂Me butyl 6-525 tert- Me S(O)Me CF₃ butyl 6-526tert- Me SMe CF₃ ¹H NMR, CDCl₃, 400 MHz butyl 12.16 (s, 1H), 7.76 (d,1H), 7.70 (d, 1H), 2.65 (s, 3H), 2.31 (s, 3H), 1.33 (s, 9H) 6-527 tert-Me SO₂CH₂CH₂OMe CF₃ butyl 6-528 tert- Me pyrazol-1-yl SO₂Me butyl 6-529tert- Me 4-methoxy- SO₂Me butyl pyrazol-1-yl 6-530 tert- Me1,2,3-triazol-1-yl SO₂Me butyl 6-531 tert- Me 1,2,3-triazol-2-yl SO₂Mebutyl 6-532 tert- Me Cl SO₂Me butyl 6-533 tert- Me Me SO₂Me butyl 6-534tert- Me Me SMe butyl 6-535 tert- Me SO₂Me Cl butyl 6-536 tert- Me NMe₂SO₂Me butyl 6-537 tert- Me NH(CH₂)₂OMe SO₂Me butyl 6-538 tert- CF₃ FSO₂CH₃ butyl 6-539 tert- CF₃ SMe SO₂CH₃ butyl 6-540 tert- CF₃ SEt SO₂CH₃butyl 6-541 tert- CF₃ S(O)Et SO₂CH₃ butyl 6-542 tert- CF₃ SO₂CH₃ SO₂CH₃butyl 6-543 tert- CF₃ OCH₂CH₂OMe SO₂CH₃ butyl 6-544 tert- CF₃OCH₂(CO)NMe₂ SO2Me butyl 6-545 tert- CF₃ CH₂O- SO₂Et butyltetrahydrofuran- 2-yl 6-546 tert- SMe SMe F butyl 6-547 tert- SMe SEt Fbutyl 6-548 tert- SO₂CH₃ F Cl butyl 6-549 tert- F S(O)Me CF₃ ¹H NMR,CDCl₃, 400 MHz butyl 9.61 (bs, 1H), 7.69 (d, 1H), 7.63 (d, 1H), 3.13 (s,3H), 1.42 (s, 9H) 6-550 tert- F SMe CF₃ butyl 6-551 furan-2-yl NO₂ HSO₂Me 6-552 furan-2-yl Cl H SO₂Me 6-553 furan-2-yl SO₂Me H CF₃ 6-554furan-2-yl NO₂ H OMe 6-555 furan-2-yl NO₂ H Br 6-556 furan-2-yl NO₂ HCF₃ 6-557 furan-2-yl NO₂ H NO₂ 6-558 furan-2-yl NO₂ H Cl 6-559furan-2-yl NO₂ H Me 6-560 furan-2-yl NO₂ H F 6-561 furan-2-yl OMe HSO₂Me 6-562 furan-2-yl CF₃ H NO₂ 6-563 furan-2-yl CH₂SO₂Me H Br 6-564furan-2-yl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.12 (dd, 1H),8.04 (d, 1H), 7.96 (d, 1H), 7.27 (bs, 1H), 6.79 (m, 1H), 5.25 (s, 3H),4.28 (q, 2H), 3.42 (s, 3H) 6-565 furan-2-yl Cl CH₂OCH₂CF₃ SMe 6-566furan-2-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 6-567furan-2- Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-568 furan-2-yl ClCH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran- 12.75 (bs, 1H),8.10 (d, 1H), 8.05 2-yl (s, 1H), 7.92 (d, 1H), 7.27 (bs, 1H), 6.79 (m,1H), 5.09 (s, 2H), 4.01-3.93 (m, 1H), 3.72 (q, 1H), 3.63-3.53 (m, 3H),3.40 (d, 3H), 1.92-1.84 (m, 1H), 1.82-1.85 (m, 2H), 1.59-1.48 (m, 1H)6-569 furan-2-yl Cl SMe Cl 6-570 furan-2-yl Cl SMe SO₂Me 6-571furan-2-yl Cl Me SO₂Et 6-572 furan-2-yl Cl O(CH₂)₂OMe Cl 6-573furan-2-yl Cl OCH₂- Cl cyclopropyl 6-574 furan-2-yl Cl OMe Cl 6-575furan-2-yl Cl NHAc Cl 6-576 furan-2-yl Cl OCH₂C(O)NMe₂ Cl 6-577furan-2-yl Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.82 (bs, 1H), 8.15 (d,1H), 8.05 (s, 1H), 7.93 (d, 1H), 7.28 (bd, 1H), 6.80 (m, 1H), 3.48 (s,3H) 6-578 furan-2-yl Cl pyrazol-1-yl SO₂Me 6-579 furan-2-yl Cl4-methoxy- SO₂Me pyrazol-1-yl 6-580 furan-2-yl Cl 1,2,3-triazol-1-ylSO₂Me 6-581 furan-2-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-582 furan-2-yl Cl FSO₂Me 6-583 furan-2-yl Me SO₂Me SO₂Me 6-584 furan-2-yl Me SO₂Me CF₃ ¹HNMR, DMSO-d₆, 400 MHz 12.63 (bs, 1H), 8.04 (m, 3H), 7.28 (bs, 1H), 6.80(m, 1H), 3.43 (s, 3H), 2.74 (s, 3H) 6-585 furan-2-yl Me NMe₂ SO₂Me 6-586furan-2-yl Me S(O)Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.39 (bs, 1H), 8.16(d, 1H), 8.05 (s, 1H), 7.98 (d, 1H), 7.59 (bs, 1H), 6.77 (m, 1H), 3.11(s, 3H), 3.09 (s, 3H) 6-587 furan-2-yl Me SMe CF₃ ¹H NMR, DMSO-d₆, 400MHz 12.47 (bs, 1H), 8.04 (d, 1H), 7.79 (d, 1H), 7.73 (d, 1H), 7.26 (bs,1H), 6.79 (m, 1H), 2.68 (s, 3H), 2.32 (s, 3H) 6-588 furan-2-yl MeSO₂CH₂CH₂OMe CF₃ 6-589 furan-2-yl Me pyrazol-1-yl SO₂Me 6-590 furan-2-ylMe 4-methoxy- SO₂Me pyrazol-1-yl 6-591 furan-2-yl Me 1,2,3-triazol-1-ylSO₂Me 6-592 furan-2-yl Me 1,2,3-triazol-2-yl SO₂Me 6-593 furan-2-yl MeCl SO₂Me 6-594 furan-2-yl Me Me SO₂Me 6-595 furan-2-yl Me Me SMe 6-596furan-2-yl Me SO₂Me Cl 6-597 furan-2-yl Me NMe₂ SO₂Me 6-598 furan-2-ylMe NH(CH₂)₂OMe SO₂Me 6-599 furan-2-yl CF₃ F SO₂CH₃ 6-600 furan-2-yl CF₃SMe SO₂CH₃ 6-601 furan-2-yl CF₃ SEt SO₂CH₃ 6-602 furan-2-yl CF₃ S(O)EtSO₂CH₃ 6-603 furan-2-yl CF₃ SO₂CH₃ SO₂CH₃ 6-604 furan-2-yl CF₃OCH₂CH₂OMe SO₂CH₃ 6-605 furan-2-yl CF₃ OCH₂(CO)NMe₂ SO2Me 6-606furan-2-yl CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl 6-607 furan-2-yl SMeSMe F 6-608 furan-2-yl SMe SEt F 6-609 furan-2-yl SO₂CH₃ F Cl 6-610furan-2-yl F S(O)Me CF₃ 6-611 furan-2-yl F SMe CF₃ 6-612 isopropyl NO₂ HSO₂Me 6-613 isopropyl Cl H SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.43 (bs,1H), 8.12 (s, 1H), 8.0 (d, 1H), 7.93 (d, 1H), 3.35 (s, 3H), 3.21-3.16(m, 1H), 1.30 (d, 6H) 6-614 isopropyl SO₂Me H CF₃ ¹H NMR, DMSO-d₆, 400MHz 8.29 (dd, 2H), 8.06 (s, 1H), 3.47 (s, 3H), 3.08 (m, 1H), 1.30 (d,6H) 6-615 isopropyl NO₂ H OMe 6-616 isopropyl NO₂ H Br 6-617 isopropylNO₂ H CF₃ 6-618 isopropyl NO₂ H NO₂ 6-619 isopropyl NO₂ H Cl 6-620isopropyl NO₂ H Me 6-621 isopropyl NO₂ H F 6-622 isopropyl OMe H SO₂Me6-623 isopropyl CF₃ H NO₂ 6-624 isopropyl CH₂SO₂Me H Br 6-625 isopropylCl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.46 (bs, 1H), 8.09 (d,1H), 7.93 (d, 1H), 5.24 (s, 2H), 4.28 (q, 2H), 3.36 (s, 3H), 3.20-3.12(m, 1H), 1.34-1.21 (m, 6H) 6-626 isopropyl Cl CH₂OCH₂CF₃ SMe 6-627isopropyl Cl 5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz4,5-dihydro-1,2- 7.92 (d, 1H), 7.78 (d, 1H), 5.18- oxazol-3-yl 5.11 (m,1H), 3.63-3.52 (m, 1H), 3.41-3.32 (m, 2H), 3.17-3.07 (m, 1H), 3.03-2.94(m, 2H), 1.31-1.19 (m, 6H), 1.10 (t, 3H) 6-628 isopropyl Cl4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-629 isopropyl Cl CH₂OCH₂- SO₂Me ¹HNMR, DMSO-d₆, 400 MHz tetrahydrofuran- 12.44 (bs, 1H), 8.07 (d, 1H),7.89 2-yl (d, 1H), 5.08 (m, 2H), 4.0-3.92 (m, 1H), 3.72 (q, 1H), 3.61(q, 1H), 3.58-3.52 (m, 2H), 3.39 (s, 3H), 3.20-3.11 (m, 1H), 1.93-1.84(m, 1H), 1.81-1.72 (m, 2H), 1.58- 1.48 (m, 1H), 1.33-1.21 (m, 6H) 6-630isopropyl Cl SMe Cl 6-631 isopropyl Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400MHz 12.52 (bs, 1H), 8.10 (d, 1H), 7.89 (d, 1H), 3.57 (s, 3H), 3.19-3.16(m, 1H), 1.30-1.28 (d, 6H) 6-632 isopropyl Cl Me SO₂Et 6-633 isopropylCl O(CH₂)₂OMe Cl 6-634 isopropyl Cl OCH₂- Cl cyclopropyl 6-635 isopropylCl OMe Cl 6-636 isopropyl Cl NHAc Cl 6-637 isopropyl Cl OCH₂C(O)NMe₂ Cl6-638 isopropyl Cl Cl SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.52 (bs, 1H),8.12 (d, 1H), 7.90 (d, 1H), 3.47 (s, 3H), 3.19-3.16 (m, 1H), 1.29 (d,6H) 6-639 isopropyl Cl pyrazol-1-yl SO₂Me 6-640 isopropyl Cl 4-methoxy-SO₂Me pyrazol-1-yl 6-641 isopropyl Cl 1,2,3-triazol-1-yl SO₂Me 6-642isopropyl Cl 1,2,3-triazol-2-yl SO₂Me 6-643 isopropyl Cl F SO₂Me 6-644isopropyl Me SO₂Me SO₂Me 6-645 isopropyl Me SO₂Me CF₃ ¹H NMR, DMSO-d₆,400 MHz 12.33 (bs, 1H), 8.0 (dd, 2H), 3.42 (s, 3H), 3.17 (m, 1H), 2.71(s, 3H), 1.37-1.24 (d, 6H) 6-646 isopropyl Me NMe₂ SO₂Me 6-647 isopropylMe S(O)Me CF₃ 6-648 isopropyl Me SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.29(bs, 1H), 7.77 (d, 1H), 7.70 (d, 1H), 3.17 (m, 1H), 2.67 (s, 3H), 2.31(s, 3H), 1.29 (d, 6H) 6-649 isopropyl Me SO₂CH₂CH₂OMe CF₃ 6-650isopropyl Me pyrazol-1-yl SO₂Me 6-651 isopropyl Me 4-methoxy- SO₂Mepyrazol-1-yl 6-652 isopropyl Me 1,2,3-triazol-1-yl SO₂Me 6-653 isopropylMe 1,2,3-triazol-2-yl SO₂Me 6-654 isopropyl Me Cl SO₂Me ¹H NMR, DMSO-d₆,400 MHz 12.32 (bs, 1H), 8.01 (d, 1H), 7.75 (d, 1H), 3.43 (s, 3H), 3.17(m, 1H), 2.46 (s, 3H), 1.30 (d, 6H) 6-655 isopropyl Me Me SO₂Me 6-656isopropyl Me F Cl ¹H NMR, DMSO-d₆, 400 MHz 12.10 (bs, 1H), 7.56 (dd,1H), 7.44 (d, 1H), 3.17 (m, 1H), 1.30 (d, 6H) 6-657 isopropyl Me SO₂MeCl 6-658 isopropyl Me NMe₂ SO₂Me 6-659 isopropyl Me NH(CH₂)₂OMe SO₂Me6-660 isopropyl CF₃ F SO₂CH₃ 6-661 isopropyl CF₃ SMe SO₂CH₃ 6-662isopropyl CF₃ SEt SO₂CH₃ 6-663 isopropyl CF₃ S(O)Et SO₂CH₃ 6-664isopropyl CF₃ SO₂CH₃ SO₂CH₃ 6-665 isopropyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-666isopropyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-667 isopropyl CF₃ CH₂O- SO₂Ettetrahydrofuran- 2-yl 6-668 isopropyl SMe SMe F 6-669 isopropyl SMe SEtF 6-670 isopropyl SO₂CH₃ F Cl 6-671 isopropyl F S(O)Me CF₃ 6-672isopropyl F SMe CF₃ 6-673 CH₂CH₂ NO₂ H SO₂Me OMe 6-674 CH₂CH₂ Cl H SO₂MeOMe 6-675 CH₂CH₂ SO₂Me H CF₃ OMe 6-676 CH₂CH₂ NO₂ H OMe OMe 6-677 CH₂CH₂NO₂ H Br OMe 6-678 CH₂CH₂ NO₂ H CF₃ OMe 6-679 CH₂CH₂ NO₂ H NO₂ OMe 6-680CH₂CH₂ NO₂ H Cl OMe 6-681 CH₂CH₂ NO₂ H Me OMe 6-682 CH₂CH₂ NO₂ H F OMe6-683 CH₂CH₂ OMe H SO₂Me OMe 6-684 CH₂CH₂ CF₃ H NO₂ OMe 6-685 CH₂CH₂CH₂SO₂Me H Br OMe 6-686 CH₂CH₂ Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400MHz OMe 12.48 (s, 1H), 8.11 (d, 1H), 7.93 (d, 1H), 5.23 (s, 2H),4.32-4.21 (m, 2H), 3.72-3.62 (m, 3H), 3.44 (s, 3H), 3.14-3.03 (m, 2H),6-687 CH₂CH₂ Cl CH₂OCH₂CF₃ SMe OMe 6-688 CH₂CH₂ Cl 5-cyanomethyl- SO₂Et¹H NMR, DMSO-d₆, 400 MHz OMe 4,5-dihydro-1,2- 8.03 (d, 1H), 7.95 (d,1H), 5.32- oxazol-3-yl 5.22 (m, 1H), 3.67 (m, 2H), 3.61- 3.53 (m, 1H),3.38 (q, 2H), 3.12 (dd, 1H), 3.08-2.98 (m, 5H), 1.20- 1.09 (m, 5H) 6-689CH₂CH₂ Cl 4,5-dihydro-1,2- SO₂Et OMe oxazol-3-yl 6-690 CH₂CH₂ ClCH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz OMe tetrahydrofuran- 12.46 (bs,1H), 8.08 (d, 1H), 7.90 2-yl (d, 1H), 5.09 (dd, 2H), 4.02-3.92 (m, 1H),3.76-3.66 (m, 3H), 3.66- 3.52 (m, 3H), 3.39 (s, 3H), 3.27 (s, 3H),3.14-3.03 (m, 2H), 1.98- 1.83 (m, 1H), 1.82-1.74 (m, 2H), 1.58-1.48 (m,1H) 6-691 CH₂CH₂ Cl SMe Cl OMe 6-692 CH₂CH₂ Cl SMe SO₂Me OMe 6-693CH₂CH₂ Cl Me SO₂Et OMe 6-694 CH₂CH₂ Cl O(CH₂)₂OMe Cl OMe 6-695 CH₂CH₂ ClOCH₂- Cl OMe cyclopropyl 6-696 CH₂CH₂ Cl OMe Cl OMe 6-697 CH₂CH₂ Cl NHAcCl OMe 6-698 CH₂CH₂ Cl OCH₂C(O)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz OMe 7.64(d, 1H), 7.46 (d, 1H), 4.72 (s, 2H), 3.68 (t, 2H), 3.26 (s, 3H), 3.07(t, 2H), 3.0 (s, 3H), 2.87 (s, 3H) 6-699 CH₂CH₂ Cl Cl SO₂Me ¹H NMR,DMSO-d₆, 400 MHz OMe 12.53 (bs, 1H), 8.13 (d, 1H), 7.90 (d, 1H), 3.69(m, 2H), 3.47 (s, 3H), 3.26 (s, 3H), 3.08 (m, 2H) 6-700 CH₂CH₂ Clpyrazol-1-yl SO₂Me OMe 6-701 CH₂CH₂ Cl 4-methoxy- SO₂Me OMe pyrazol-1-yl6-702 CH₂CH₂ Cl 1,2,3-triazol-1-yl SO₂Me OMe 6-703 CH₂CH₂ Cl1,2,3-triazol-2-yl SO₂Me OMe 6-704 CH₂CH₂ Cl F SO₂Me OMe 6-705 CH₂CH₂ MeSO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz OMe 8.15 (d, 1H), 7.91 (d, 1H),3.66 (m, 2H), 3.57 (s, 3H), 3.53 (s, 3H), 3.24 (s, 3H), 6-706 CH₂CH₂ MeSO₂Me CF₃ OMe 6-707 CH₂CH₂ Me NMe₂ SO₂Me OMe 6-708 CH₂CH₂ Me S(O)Me CF₃OMe 6-709 CH₂CH₂ Me SMe CF₃ OMe 6-710 CH₂CH₂ Me SO₂CH₂CH₂OMe CF₃ OMe6-711 CH₂CH₂ Me pyrazol-1-yl SO₂Me OMe 6-712 CH₂CH₂ Me 4-methoxy- SO₂MeOMe pyrazol-1-yl 6-713 CH₂CH₂ Me 1,2,3-triazol-1-yl SO₂Me OMe 6-714CH₂CH₂ Me 1,2,3-triazol-2-yl SO₂Me OMe 6-715 CH₂CH₂ Me Cl SO₂Me OMe6-716 CH₂CH₂ Me Me SO₂Me OMe 6-717 CH₂CH₂ Me Me SMe OMe 6-718 CH₂CH₂ MeSO₂Me Cl OMe 6-719 CH₂CH₂ Me NMe₂ SO₂Me OMe 6-720 CH₂CH₂ Me NH(CH₂)₂OMeSO₂Me OMe 6-721 CH₂CH₂ CF₃ F SO₂CH₃ OMe 6-722 CH₂CH₂ CF₃ SMe SO₂CH₃ OMe6-723 CH₂CH₂ CF₃ SEt SO₂CH₃ OMe 6-724 CH₂CH₂ CF₃ S(O)Et SO₂CH₃ OMe 6-725CH₂CH₂ CF₃ SO₂CH₃ SO₂CH₃ OMe 6-726 CH₂CH₂ CF₃ OCH₂CH₂OMe SO₂CH₃ OMe6-727 CH₂CH₂ CF₃ OCH₂(CO)NMe₂ SO2Me OMe 6-728 CH₂CH₂ CF₃ CH₂O- SO₂Et OMetetrahydrofuran- 2-yl 6-729 CH₂CH₂ SMe SMe F OMe 6-730 CH₂CH₂ SMe SEt FOMe 6-731 CH₂CH₂ SO₂CH₃ F Cl OMe 6-732 CH₂CH₂ F S(O)Me CF₃ OMe 6-733CH₂CH₂ F SMe CF₃ OMe 6-734 CH₂CF₃ NO₂ H SO₂Me 6-735 CH₂CF₃ Cl H SO₂Me6-736 CH₂CF₃ SO₂Me H CF₃ 6-737 CH₂CF₃ NO₂ H OMe 6-738 CH₂CF₃ NO₂ H Br6-739 CH₂CF₃ NO₂ H CF₃ 6-740 CH₂CF₃ NO₂ H NO₂ 6-741 CH₂CF₃ NO₂ H Cl6-742 CH₂CF₃ NO₂ H Me 6-743 CH₂CF₃ NO₂ H F 6-744 CH₂CF₃ OMe H SO₂Me6-745 CH₂CF₃ CF₃ H NO₂ 6-746 CH₂CF₃ CH₂SO₂Me H Br 6-747 CH₂CF₃ ClCH₂OCH₂CF₃ SO₂Me 6-748 CH₂CF₃ Cl CH₂OCH₂CF₃ SMe 6-749 CH₂CF₃ Cl5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 4,5-dihydro-1,2- 12.78(bs, 1H), 8.10 (2d, 2H), oxazol-3-yl 5.19 (m, 1H), 4.33 (q, 2H), 3.61(m, 1H), 3.44 (q, 2H), 3.16 (dd, 1H), 3.08 (d, 2H), 1.16 (t, 3H) 6-750CH₂CF₃ Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-751 CH₂CF₃ Cl CH₂OCH₂-SO₂Me tetrahydrofuran- 2-yl 6-752 CH₂CF₃ Cl SMe Cl 6-753 CH₂CF₃ Cl SMeSO₂Me ¹H NMR, DMSO-d₆, 400 MHz 8.21 (d, 1H), 8.16 (d, 1H), 3.74 (q, 2H),3.60 (s, 3H) 6-754 CH₂CF₃ Cl Me SO₂Et 6-755 CH₂CF₃ Cl O(CH₂)₂OMe Cl6-756 CH₂CF₃ Cl OCH₂- Cl cyclopropyl 6-757 CH₂CF₃ Cl OMe Cl 6-758 CH₂CF₃Cl NHAc Cl 6-759 CH₂CF₃ Cl OCH₂C(O)NMe₂ Cl 6-760 CH₂CF₃ Cl Cl SO₂Me6-761 CH₂CF₃ Cl pyrazol-1-yl SO₂Me 6-762 CH₂CF₃ Cl 4-methoxy- SO₂Mepyrazol-1-yl 6-763 CH₂CF₃ Cl 1,2,3-triazol-1-yl SO₂Me 6-764 CH₂CF₃ Cl1,2,3-triazol-2-yl SO₂Me 6-765 CH₂CF₃ Cl F SO₂Me 6-766 CH₂CF₃ Me SO₂MeSO₂Me 6-767 CH₂CF₃ Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.62 (bs, 1H),8.02 (dd, 2H), 4.31 (q, 2H), 3.43 (s, 3H), 2.62 (s, 3H) 6-768 CH₂CF₃ MeNMe₂ SO₂Me 6-769 CH₂CF₃ Me S(O)Me CF₃ 6-770 CH₂CF₃ Me SMe CF₃ ¹H NMR,DMSO-d₆, 400 MHz 12.41 (bs, 1H), 7.78 (d, 1H), 7.32 (d, 1H), 4.31 (q,2H), 2.67 (s, 3H), 2.31 (s, 3H) 6-771 CH₂CF₃ Me SO₂CH₂CH₂OMe CF₃ 6-772CH₂CF₃ Me pyrazol-1-yl SO₂Me 6-773 CH₂CF₃ Me 4-methoxy- SO₂Mepyrazol-1-yl 6-774 CH₂CF₃ Me 1,2,3-triazol-1-yl SO₂Me 6-775 CH₂CF₃ Me1,2,3-triazol-2-yl SO₂Me 6-776 CH₂CF₃ Me Cl SO₂Me 6-777 CH₂CF₃ Me MeSO₂Me 6-778 CH₂CF₃ Me Me SMe 6-779 CH₂CF₃ Me SO₂Me Cl 6-780 CH₂CF₃ MeNMe₂ SO₂Me 6-781 CH₂CF₃ Me NH(CH₂)₂OMe SO₂Me 6-782 CH₂CF₃ CF₃ F SO₂CH₃6-783 CH₂CF₃ CF₃ SMe SO₂CH₃ 6-784 CH₂CF₃ CF₃ SEt SO₂CH₃ 6-785 CH₂CF₃ CF₃S(O)Et SO₂CH₃ 6-786 CH₂CF₃ CF₃ SO₂CH₃ SO₂CH₃ 6-787 CH₂CF₃ CF₃ OCH₂CH₂OMeSO₂CH₃ 6-788 CH₂CF₃ CF₃ OCH₂(CO)NMe₂ SO2Me 6-789 CH₂CF₃ CF₃ CH₂O- SO₂Ettetrahydrofuran- 2-yl 6-790 CH₂CF₃ SMe SMe F 6-791 CH₂CF₃ SMe SEt F6-792 CH₂CF₃ SO₂CH₃ F Cl 6-793 CH₂CF₃ F S(O)Me CF₃ 6-794 CH₂CF₃ F SMeCF₃ 6-795 tetrahydro- NO₂ H SO₂Me furan-2-yl 6-796 tetrahydro- Cl HSO₂Me furan-2-yl 6-797 tetrahydro- SO₂Me H CF₃ furan-2-yl 6-798tetrahydro- NO₂ H OMe furan-2-yl 6-799 tetrahydro- NO₂ H Br furan-2-yl6-800 tetrahydro- NO₂ H CF₃ furan-2-yl 6-801 tetrahydro- NO₂ H NO₂furan-2-yl 6-802 tetrahydro- NO₂ H Cl furan-2-yl 6-803 tetrahydro- NO₂ HMe furan-2-yl 6-804 tetrahydro- NO₂ H F furan-2-yl 6-805 tetrahydro- OMeH SO₂Me furan-2-yl 6-806 tetrahydro- CF₃ H NO₂ furan-2-yl 6-807tetrahydro- CH₂SO₂Me H Br furan-2-yl 6-808 tetrahydro- Cl CH₂OCH₂CF₃SO₂Me furan-2-yl 6-809 tetrahydro- Cl CH₂OCH₂CF₃ SMe furan-2-yl 6-810tetrahydro- Cl 5-cyanomethyl- SO₂Et furan-2-yl 4,5-dihydro-1,2-oxazol-3-yl 6-811 tetrahydro- Cl 4,5-dihydro-1,2- SO₂Et furan-2-yloxazol-3-yl 6-812 tetrahydro- Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHzfuran-2-yl tetrahydrofuran- 12.60 (bs, 1H), 8.08 (d, 1H), 7.89 2-yl (d,1H), 5.10 (m, 2H), 3.97 (m, 1H), 3.38 (s, 3H), 6-813 tetrahydro- Cl SMeCl furan-2-yl 6-814 tetrahydro- Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHzfuran-2-yl 12.60 (bs, 1H), 8.11 (d, 1H), 7.90 (d, 1H), 5.11 (m, 1H),3.84 (m, 2H), 3.58 (s, 3H), 2.26 (m, 2H), 1.98 (m, 2H) 6-815 tetrahydro-Cl Me SO₂Et furan-2-yl 6-816 tetrahydro- Cl O(CH₂)₂OMe Cl furan-2-yl6-817 tetrahydro- Cl OCH₂- Cl furan-2-yl cyclopropyl 6-818 tetrahydro-Cl OMe Cl furan-2-yl 6-819 tetrahydro- Cl NHAc Cl furan-2-yl 6-820tetrahydro- Cl OCH₂C(O)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz furan-2-yl 12.44(bs, 1H), 7.64 (d, 1H), 7.47 (d, 1H), 5.11 (dd, 1H), 4.72 (s, 2H), 3.84(t, 2H), 3.01 (s, 3H), 2.87 (s, 3H), 2.32-2.21 (m, 2H), 2.04-1.95 (m,2H) 6-821 tetrahydro- Cl Cl SO₂Me furan-2-yl 6-822 tetrahydro- Clpyrazol-1-yl SO₂Me furan-2-yl 6-823 tetrahydro- Cl 4-methoxy- SO₂Mefuran-2-yl pyrazol-1-yl 6-824 tetrahydro- Cl 1,2,3-triazol-1-yl SO₂Mefuran-2-yl 6-825 tetrahydro- Cl 1,2,3-triazol-2-yl SO₂Me furan-2-yl6-826 tetrahydro- Cl F SO₂Me furan-2-yl 6-827 tetrahydro- Me SO₂Me SO₂Mefuran-2-yl 6-828 tetrahydro- Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHzfuran-2-yl 12.5 (bs, 1H), 7.99 (dd, 2H), 5.11 (m, 1H), 3.84 (m, 2H),3.41 (s, 3H), 2.71 (s, 3H), 2.32-2.21 (m, 2H), 2.04-1.93 (m, 2H) 6-829tetrahydro- Me NMe₂ SO₂Me furan-2-yl 6-830 tetrahydro- Me S(O)Me CF₃furan-2-yl 6-831 tetrahydro- Me SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHzfuran-2-yl 12.31 (bs, 1H), 7.77 (d, 1H), 7.70 (d, 1H), 5.11 (dd, 1H),3.84 (dd, 2H), 2.67 (s, 3H), 2.28 (s, 3H), 2.37-2.20 (m, 2H), 2.07-1.95(m, 2H) 6-832 tetrahydro- Me SO₂CH₂CH₂OMe CF₃ furan-2-yl 6-833tetrahydro- Me pyrazol-1-yl SO₂Me furan-2-yl 6-834 tetrahydro- Me4-methoxy- SO₂Me furan-2-yl pyrazol-1-yl 6-835 tetrahydro- Me1,2,3-triazol-1-yl SO₂Me furan-2-yl 6-836 tetrahydro- Me1,2,3-triazol-2-yl SO₂Me furan-2-yl 6-837 tetrahydro- Me Cl SO₂Mefuran-2-yl 6-838 tetrahydro- Me Me SO₂Me furan-2-yl 6-839 tetrahydro- MeMe SMe furan-2-yl 6-840 tetrahydro- Me SO₂Me Cl furan-2-yl 6-841tetrahydro- Me NMe₂ SO₂Me furan-2-yl 6-842 tetrahydro- Me NH(CH₂)₂OMeSO₂Me furan-2-yl 6-843 tetrahydro- CF₃ F SO₂CH₃ furan-2-yl 6-844tetrahydro- CF₃ SMe SO₂CH₃ furan-2-yl 6-845 tetrahydro- CF₃ SEt SO₂CH₃furan-2-yl 6-846 tetrahydro- CF₃ S(O)Et SO₂CH₃ furan-2-yl 6-847tetrahydro- CF₃ SO₂CH₃ SO₂CH₃ furan-2-yl 6-848 tetrahydro- CF₃OCH₂CH₂OMe SO₂CH₃ furan-2-yl 6-849 tetrahydro- CF₃ OCH₂(CO)NMe₂ SO₂Mefuran-2-yl 6-850 tetrahydro- CF₃ CH₂O- SO₂Et furan-2-yl tetrahydrofuran-2-yl 6-851 tetrahydro- SMe SMe F furan-2-yl 6-852 tetrahydro- SMe SEt Ffuran-2-yl 6-853 tetrahydro- SO₂CH₃ F Cl furan-2-yl 6-854 tetrahydro- FS(O)Me CF₃ furan-2-yl 6-855 tetrahydro- F SMe CF₃ furan-2-yl 6-856 n-PrNO₂ H SO₂Me 6-857 n-Pr Cl H SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.41 (s,1H), 8.11 (d, 1H), 7.97 (dd, 1H), 7.93 (d, 1H), 3.38 (s, 3H), 2.80 (t,2H), 1.70 (m, 2H), 0.92 (t, 3H) 6-858 n-Pr SO₂Me H CF₃ ¹H NMR, DMSO-d₆,400 MHz 8.27 (dd, 2H), 8.04 (s, 1H), 3.48 (s, 3H), 2.80 (m, 2H), 1.72(m, 2H), 0.97 (m, 3H) 6-859 n-Pr NO₂ H OMe 6-860 n-Pr NO₂ H Br 6-861n-Pr NO₂ H Cl 6-862 n-Pr NO₂ H CF₃ 6-863 n-Pr NO₂ H NO₂ 6-864 n-Pr NO₂ HMe 6-865 n-Pr NO₂ H F 6-866 n-Pr OMe H SO₂Me 6-867 n-Pr CF₃ H NO₂ 6-868n-Pr CH₂SO₂Me H Br 6-869 n-Pr Cl CH₂OCH₂CF₃ SO₂Me 6-870 n-Pr ClCH₂OCH₂CF₃ SMe ¹H NMR, DMSO-d₆, 400 MHz 11.34 (bs, 1H), 7.63 (d, 1H),7.45 (d, 1H), 4.92 (s, 2H), 4.20 (q, 2H), 2.78 (t, 2H), 1.71 (m, 2H),0.94 (t, 3H) 6-871 n-Pr Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-872 n-Pr Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-873 n-PrCl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran- 12.46 (bs,1H), 8.08 (d, 1H), 7.89 2-yl (d, 1H), 5.07 (d, 2H), 3.97 (m, 1H), 3.72(q, 1H), 3.62 (q, 1H), 3.56 (m, 2H), 3.39 (s, 3H), 2.81 (t, 2H),1.96-1.87 (m, 1H), 1.83- 1.76 (m, 2H), 1.76-1.66 (m, 2H), 1.58-1.49 (m,1H), 0.96 (t, 3H) 6-874 n-Pr Cl SMe Cl 6-875 n-Pr Cl SMe SO₂Me ¹H NMR,DMSO-d₆, 400 MHz 12.45 (bs, 1H), 8.10 (d, 1H), 7.89 (d, 1H), 3.57 (s,3H), 2.80 (t, 2H), 1.70 (m, 2H), 0.95 (t, 3H) 6-876 n-Pr Cl Me SO₂Et6-877 n-Pr Cl O(CH₂)₂OMe Cl 6-878 n-Pr Cl OCH₂- Cl cyclopropyl 6-879n-Pr Cl OMe Cl 6-880 n-Pr Cl NHAc Cl 6-881 n-Pr Cl OCH₂C(O)NMe₂ Cl ¹HNMR, DMSO-d₆, 400 MHz 12.29 (bs, 1H), 7.62 (d, 1H), 7.46 (d, 1H), 4.72(s, 2H), 3.01 (s, 3H), 2.87 (s, 3H), 2.80 (t, 2H), 1.71 (m, 2H), 0.96(t, 3H) 6-882 n-Pr Cl Cl SO₂Me 6-883 n-Pr Cl pyrazol-1-yl SO₂Me 6-884n-Pr Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-885 n-Pr Cl 1,2,3-triazol-1-ylSO₂Me 6-886 n-Pr Cl 1,2,3-triazol-2-yl SO₂Me 6-887 n-Pr Cl F SO₂Me 6-888n-Pr Me SO₂Me SO₂Me 6-889 n-Pr Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz12.35 (bs, 1H), 8.0 (dd, 2H), 3.42 (s, 3H), 2.81-2.75 (m, 2H), 2.71 (s,3H), 1.78-1.64 (m, 2H), 0.96 (t, 3H) 6-890 n-Pr Me NMe₂ SO₂Me 6-891 n-PrMe S(O)Me CF₃ 6-892 n-Pr Me SMe CF₃ ¹H NMR, DMSO-d₆, 400 MHz 12.20 (bs,1H), 7.77 (d, 1H), 7.69 (d, 1H), 2.80 (t, 2H), 2.67 (s, 3H), 2.33 (s,3H), 1.73-1.68 (m, 2H), 0.96 (t, 3H) 6-893 n-Pr Me SO₂CH₂CH₂OMe CF₃6-894 n-Pr Me pyrazol-1-yl SO₂Me 6-895 n-Pr Me 4-methoxy- SO₂Mepyrazol-1-yl 6-896 n-Pr Me 1,2,3-triazol-1-yl SO₂Me 6-897 n-Pr Me1,2,3-triazol-2-yl SO₂Me 6-898 n-Pr Me Cl SO₂Me 6-899 n-Pr Me Me SO₂Me6-900 n-Pr Me Me SMe 6-901 n-Pr Me SO₂Me Cl 6-902 n-Pr Me NMe₂ SO₂Me6-903 n-Pr Me NH(CH₂)₂OMe SO₂Me 6-904 n-Pr CF₃ F SO₂CH₃ 6-905 n-Pr CF₃SMe SO₂CH₃ 6-906 n-Pr CF₃ SEt SO₂CH₃ 6-907 n-Pr CF₃ S(O)Et SO₂CH₃ 6-908n-Pr CF₃ SO₂CH₃ SO₂CH₃ 6-909 n-Pr CF₃ OCH₂CH₂OMe SO₂CH₃ 6-910 n-Pr CF₃OCH₂(CO)NMe₂ SO2Me 6-911 n-Pr CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl6-912 n-Pr SMe SMe F 6-913 n-Pr SMe SEt F 6-914 n-Pr SO₂CH₃ F Cl 6-915n-Pr F S(O)Me CF₃ 6-916 n-Pr F SMe CF₃ 6-917 CH₂OEt NO₂ H SO₂Me 6-918CH₂OEt Cl H SO₂Me 6-919 CH₂OEt SO₂Me H CF₃ 6-920 CH₂OEt NO₂ H OMe 6-921CH₂OEt NO₂ H Br 6-922 CH₂OEt NO₂ H CF₃ 6-923 CH₂OEt NO₂ H NO₂ 6-924CH₂OEt NO₂ H Cl 6-925 CH₂OEt NO₂ H Me 6-926 CH₂OEt NO₂ H F 6-927 CH₂OEtOMe H SO₂Me 6-928 CH₂OEt CF₃ H NO₂ 6-929 CH₂OEt CH₂SO₂Me H Br 6-930CH₂OEt Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.63 (bs, 1H), 8.11(d, 1H), 7.96 (d, 1H), 5.24 (s, 2H), 4.66 (s, 2H), 4.29 (q, 2H), 3.55(q, 2H), 1.15 (t, 3H) 6-931 CH₂OEt Cl CH₂OCH₂CF₃ SMe 6-932 CH₂OEt Cl5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz 4,5-dihydro-1,2- 12.69(bs, 1H), 8.11 (d, 1H), 8.08 oxazol-3-yl (d, 1H), 5.21-5.17 (m, 1H),4.66 (s, 2H), 3.64-3.52 (m, 4H), 3.42 (q, 2H), 3.16 (dd, 1H), 3.02 (m,2H), 1.16 (2t, 6H) 6-933 CH₂OEt Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl6-934 CH₂OEt Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-935 CH₂OEt Cl SMeCl 6-936 CH₂OEt Cl SMe SO₂Me 6-937 CH₂OEt Cl Me SO₂Et 6-938 CH₂OEt ClO(CH₂)₂OMe Cl 6-939 CH₂OEt Cl OCH₂- Cl cyclopropyl 6-940 CH₂OEt Cl OMeCl 6-941 CH₂OEt Cl NHAc Cl 6-942 CH₂OEt Cl OCH₂C(O)NMe₂ Cl 6-943 CH₂OEtCl Cl SO₂Me 6-944 CH₂OEt Cl pyrazol-1-yl SO₂Me 6-945 CH₂OEt Cl4-methoxy- SO₂Me pyrazol-1-yl 6-946 CH₂OEt Cl 1,2,3-triazol-1-yl SO₂Me6-947 CH₂OEt Cl 1,2,3-triazol-2-yl SO₂Me 6-948 CH₂OEt Cl F SO₂Me 6-949CH₂OEt Me SO₂Me SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.58 (bs, 1H), 8.24 (d,1H), 8.06 (d, 1H), 4.66 (s, 2H), 3.60 (s, 3H), 3.55 (s, 3H), 2.69 (s,3H), 1.16 (t, 3H) 6-950 CH₂OEt Me SO₂Me CF₃ ¹H NMR, DMSO-d₆, 400 MHz12.50 (bs, 1H), 8.03 (d, 1H), 8.00 (d, 1H), 4.66 (s, 2H), 3.56 (q, 2H),3.42 (s, 3H), 2.72 (s, 3H), 1.16 (t, 3H) 6-951 CH₂OEt Me NMe₂ SO₂Me6-952 CH₂OEt Me S(O)Me CF₃ 6-953 CH₂OEt Me SMe CF₃ 6-954 CH₂OEt MeSO₂CH₂CH₂OMe CF₃ 6-955 CH₂OEt Me pyrazol-1-yl SO₂Me 6-956 CH₂OEt Me4-methoxy- SO₂Me pyrazol-1-yl 6-957 CH₂OEt Me 1,2,3-triazol-1-yl SO₂Me6-958 CH₂OEt Me 1,2,3-triazol-2-yl SO₂Me 6-959 CH₂OEt Me Cl SO₂Me 6-960CH₂OEt Me Me SO₂Me 6-961 CH₂OEt Me Me SMe 6-962 CH₂OEt Me SO₂Me Cl 6-963CH₂OEt Me NMe₂ SO₂Me 6-964 CH₂OEt Me NH(CH₂)₂OMe SO₂Me 6-965 CH₂OEt CF₃F SO₂CH₃ 6-966 CH₂OEt CF₃ SMe SO₂CH₃ 6-967 CH₂OEt CF₃ SEt SO₂CH₃ 6-968CH₂OEt CF₃ S(O)Et SO₂CH₃ 6-969 CH₂OEt CF₃ SO₂CH₃ SO₂CH₃ 6-970 CH₂OEt CF₃OCH₂CH₂OMe SO₂CH₃ 6-971 CH₂OEt CF₃ OCH₂(CO)NMe₂ SO2Me 6-972 CH₂OEt CF₃CH₂O- SO₂Et tetrahydrofuran- 2-yl 6-973 CH₂OEt SMe SMe F 6-974 CH₂OEtSMe SEt F 6-975 CH₂OEt SO₂CH₃ F Cl 6-976 CH₂OEt F S(O)Me CF₃ 6-977CH₂OEt F SMe CF₃ 6-978 cyclobutyl NO₂ H SO₂Me 6-979 cyclobutyl Cl HSO₂Me 6-980 cyclobutyl SO₂Me H CF₃ 6-981 cyclobutyl NO₂ H OMe 6-982cyclobutyl NO₂ H Br 6-983 cyclobutyl SMe H CF₃ ¹H NMR, DMSO-d₆, 400 MHz12.19 (bs, 1H), 7.91 (bs, 1H), 7.64 (d, 1H), 7.61 (d, 1H), 3.77- 3.69(m, 1H), 2.54 (s, 3H), 2.40- 2.22 (m, 4H), 2.10-1.85 (m, 2H) 6-984cyclobutyl NO₂ H NO₂ 6-985 cyclobutyl NO₂ H Cl 6-986 cyclobutyl NO₂ H Me6-987 cyclobutyl NO₂ H F 6-988 cyclobutyl OMe H SO₂Me 6-989 cyclobutylCF₃ H NO₂ 6-990 cyclobutyl CH₂SO₂Me H Br 6-991 cyclobutyl Cl CH₂OCH₂CF₃SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.49 (s, 1H), 8.09 (d, 1H), 7.93 (d,1H), 5.24 (s, 2H), 4.28 (q, 2H), 3.72 (m, 1H), 3.34 (s, 3H), 2.40-2.22(m, 4H), 2.10-2.02 (m, 1H), 1.98-1.89 (m, 1H) 6-992 cyclobutyl ClCH₂OCH₂CF₃ SMe 6-993 cyclobutyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 6-994 cyclobutyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-995cyclobutyl Cl CH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran-12.45 (s, 1H), 8.09 (d, 1H), 7.88 2-yl (d, 1H), 5.07 (s, 2H), 3.96 (m,1H), 3.71 (m, 2H), 3.66-3.51 (m, 3H), 3.48 (s, 3H), 2.40-2.25 (m, 4H),2.10-1.71 (m, 5H), 1.59- 1.49 (m, 1H) 6-996 cyclobutyl Cl SMe Cl 6-997cyclobutyl Cl SMe SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.43 (s, 1H), 8.10 (d,1H), 7.89 (d, 1H), 3.73 (t, 1H), 3.57 (s, 3H), 2.40-2.25 (m, 4H),2.10-2.02 (m, 1H), 1.98-1.88 (m, 1H) 6-998 cyclobutyl Cl Me SO₂Et 6-999cyclobutyl Cl O(CH₂)₂OMe Cl 6-1000 cyclobutyl Cl OCH₂- Cl cyclopropyl6-1001 cyclobutyl Cl OMe Cl 6-1002 cyclobutyl Cl NHAc Cl 6-1003cyclobutyl Cl OCH₂C(O)NMe₂ Cl 6-1004 cyclobutyl Cl Cl SO₂Me 6-1005cyclobutyl Cl pyrazol-1-yl SO₂Me 6-1006 cyclobutyl Cl 4-methoxy- SO₂Mepyrazol-1-yl 6-1007 cyclobutyl Cl 1,2,3-triazol-1-yl SO₂Me 6-1008cyclobutyl Cl 1,2,3-triazol-2-yl SO₂Me 6-1009 cyclobutyl Cl F SO₂Me6-1010 cyclobutyl Me SO₂Me SO₂Me 6-1011 cyclobutyl Me SO₂Me CF₃ ¹H NMR,DMSO-d₆, 400 MHz 12.37 (s, 1H), 8.01 (d, 1H), 7.97 (d, 1H), 3.73 (t,1H), 3.40 (s, 3H), 2.70 (s, 3H), 2.39-2.24 (m, 4H), 2.09-2.02 (m, 1H),1.98-1.86 (m, 1H) 6-1012 cyclobutyl Me NMe₂ SO₂Me 6-1013 cyclobutyl MeS(O)Me CF₃ 6-1014 cyclobutyl Me SMe CF₃ 6-1015 cyclobutyl MeSO₂CH₂CH₂OMe CF₃ 6-1016 cyclobutyl Me pyrazol-1-yl SO₂Me 6-1017cyclobutyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1018 cyclobutyl Me1,2,3-triazol-1-yl SO₂Me 6-1019 cyclobutyl Me 1,2,3-triazol-2-yl SO₂Me6-1020 cyclobutyl Me Cl SO₂Me 6-1021 cyclobutyl Me Me SO₂Me 6-1022cyclobutyl Me Me SMe 6-1023 cyclobutyl Me SO₂Me Cl 6-1024 cyclobutyl MeNMe₂ SO₂Me 6-1025 cyclobutyl Me NH(CH₂)₂OMe SO₂Me 6-1026 cyclobutyl CF₃F SO₂CH₃ 6-1027 cyclobutyl CF₃ SMe SO₂CH₃ 6-1028 cyclobutyl CF₃ SEtSO₂CH₃ 6-1029 cyclobutyl CF₃ S(O)Et SO₂CH₃ 6-1030 cyclobutyl CF₃ SO₂CH₃SO₂CH₃ 6-1031 cyclobutyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1032 cyclobutyl CF₃OCH₂(CO)NMe₂ SO2Me 6-1033 cyclobutyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1034 cyclobutyl SMe SMe F 6-1035 cyclobutyl SMe SEt F 6-1036cyclobutyl SO₂CH₃ F Cl 6-1037 cyclobutyl F S(O)Me CF₃ 6-1038 cyclobutylF SMe CF₃ 6-1039 cyclopentyl NO₂ H SO₂Me 6-1040 cyclopentyl Cl H SO₂Me6-1041 cyclopentyl SO₂Me H CF₃ 6-1042 cyclopentyl NO₂ H OMe 6-1043cyclopentyl NO₂ H Br 6-1044 cyclopentyl SMe H CF₃ ¹H NMR, DMSO-d₆, 400MHz 12.16 (bs, 1H), 7.83 (bs, 1H), 7.64 (d, 1H), 7.61 (d, 1H), 2.56 (s,3H), 2.09-1.97 (m, 2H), 1.87- 75 (m, 2H), 1.72-1.60 (m, 4H) 6-1045cyclopentyl NO₂ H NO₂ 6-1046 cyclopentyl NO₂ H Cl 6-1047 cyclopentyl NO₂H Me 6-1048 cyclopentyl NO₂ H F 6-1049 cyclopentyl OMe H SO₂Me 6-1050cyclopentyl CF₃ H NO₂ 6-1051 cyclopentyl CH₂SO₂Me H Br 6-1052cyclopentyl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 12.47 (s, 1H),8.09 (d, 1H), 7.92 (d, 1H), 5.24 (s, 2H), 4.28 (q, 2H), 3.39 (s, 3H),207-1.96 (m, 2H), 1.85-1.56 (m, 6H) 6-1053 cyclopentyl Cl CH₂OCH₂CF₃ SMe6-1054 cyclopentyl Cl 5-cyanomethyl- SO₂Et ¹H NMR, DMSO-d₆, 400 MHz4,5-dihydro-1,2- 12.45 (s, 1H), 8.09 (d, 1H), 8.06 oxazol-3-yl (d, 1H),5.22-5.15 (m, 1H), 3.59 (dd, 1H), 3.42 (q, 2H), 3.14 (dd, 1H), 3.02 (m,2H), 2.09-1.97 (m, 2H), 1.87-1.60 (m, 6H), 1.16 (t, 3H) 6-1055cyclopentyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-1056 cyclopentyl ClCH₂OCH₂- SO₂Me ¹H NMR, DMSO-d₆, 400 MHz tetrahydrofuran- 12.45 (s, 1H),8.07 (d, 1H), 7.88 2-yl (d, 1H), 5.07 (dd, 2H), 3.98 (m, 1H), 3.71 (dd,1H), 3.64-3.51 (m, 3H), 3.49 (s, 3H), 2.08-1.47 (m, 12H), 6-1057cyclopentyl Cl SMe Cl 6-1058 cyclopentyl Cl SMe SO₂Me ¹H NMR, DMSO-d₆,400 MHz 12.42 (s, 1H), 8.10 (d, 1H), 7.88 (d, 1H), 3.57 (s, 3H), 2.55(s, 3H), 2.07-1.96 (m, 2H), 1.88- 1.46 (m, 6H) 6-1059 cyclopentyl Cl MeSO₂Et 6-1060 cyclopentyl Cl O(CH₂)₂OMe Cl 6-1061 cyclopentyl Cl OCH₂- Clcyclopropyl 6-1062 cyclopentyl Cl OMe Cl 6-1063 cyclopentyl Cl NHAc Cl6-1064 cyclopentyl Cl OCH₂C(O)NMe₂ Cl ¹H NMR, DMSO-d₆, 400 MHz 12.23 (s,1H), 7.62 (d, 1H), 7.45 (d, 1H), 4.72 (s, 3H), 2.99 (s, 3H), 2.86 (s,3H), 2.08-1.98 (m, 2H), 1.82-1.73 (m, 2H), 1.70-1.49 (m, 4H) 6-1065cyclopentyl Cl Cl SO₂Me 6-1066 cyclopentyl Cl pyrazol-1-yl SO₂Me 6-1067cyclopentyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1068 cyclopentyl Cl1,2,3-triazol-1-yl SO₂Me 6-1069 cyclopentyl Cl 1,2,3-triazol-2-yl SO₂Me6-1070 cyclopentyl Cl F SO₂Me 6-1071 cyclopentyl Me SO₂Me SO₂Me 6-1072cyclopentyl Me SO₂Me CF₃ 6-1073 cyclopentyl Me NMe₂ SO₂Me 6-1074cyclopentyl Me S(O)Me CF₃ ¹H NMR, CDCl₃, 400 MHz 10.85 (s, 1H), 8.18(dd, 2H), 7.63 (d, 2H), 7.39 (dd, 2H), 7.05 (dd, 1H), 5.30 (s, 2H), 4.32(q, 2H), 3.39 (s, 3H) 6-1075 cyclopentyl Me SMe CF₃ 6-1076 cyclopentylMe SO₂CH₂CH₂OMe CF₃ 6-1077 cyclopentyl Me pyrazol-1-yl SO₂Me 6-1078cyclopentyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1079 cyclopentyl Me1,2,3-triazol-1-yl SO₂Me 6-1080 cyclopentyl Me 1,2,3-triazol-2-yl SO₂Me6-1081 cyclopentyl Me Cl SO₂Me 6-1082 cyclopentyl Me Me SO₂Me 6-1083cyclopentyl Me Me SMe 6-1084 cyclopentyl Me SO₂Me Cl 6-1085 cyclopentylMe NMe₂ SO₂Me 6-1086 cyclopentyl Me NH(CH₂)₂OMe SO₂Me 6-1087 cyclopentylCF₃ F SO₂CH₃ 6-1088 cyclopentyl CF₃ SMe SO₂CH₃ 6-1089 cyclopentyl CF₃SEt SO₂CH₃ 6-1090 cyclopentyl CF₃ S(O)Et SO₂CH₃ 6-1091 cyclopentyl CF₃SO₂CH₃ SO₂CH₃ 6-1092 cyclopentyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1093cyclopentyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-1094 cyclopentyl CF₃ CH₂O- SO₂Ettetrahydrofuran- 2-yl 6-1095 cyclopentyl SMe SMe F 6-1096 cyclopentylSMe SEt F 6-1097 cyclopentyl SO₂CH₃ F Cl 6-1098 cyclopentyl F S(O)Me CF₃6-1099 cyclopentyl F SMe CF₃ 6-1100 Me₂N NO₂ H SO₂Me 6-1101 Me₂N Cl HSO₂Me 6-1102 Me₂N SO₂Me H CF₃ 6-1103 Me₂N NO₂ H OMe 6-1104 Me₂N NO₂ H Br6-1105 Me₂N NO₂ H CF₃ 6-1106 Me₂N NO₂ H NO₂ 6-1107 Me₂N NO₂ H Cl 6-1108Me₂N NO₂ H Me 6-1109 Me₂N NO₂ H F 6-1110 Me₂N OMe H SO₂Me 6-1111 Me₂NCF₃ H NO₂ 6-1112 Me₂N CH₂SO₂Me H Br 6-1113 Me₂N Cl CH₂OCH₂CF₃ SO₂Me6-1114 Me₂N Cl CH₂OCH₂CF₃ SMe 6-1115 Me₂N Cl 5-cyanomethyl- SO₂Et4,5-dihydro-1,2- oxazol-3-yl 6-1116 Me₂N Cl 4,5-dihydro-1,2- SO₂Etoxazol-3-yl 6-1117 Me₂N Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-1118Me₂N Cl SMe Cl 6-1119 Me₂N Cl SMe SO₂Me 6-1120 Me₂N Cl Me SO₂Et 6-1121Me₂N Cl O(CH₂)₂OMe Cl 6-1122 Me₂N Cl OCH₂- Cl cyclopropyl 6-1123 Me₂N ClOMe Cl 6-1124 Me₂N Cl NHAc Cl 6-1125 Me₂N Cl OCH₂C(O)NMe₂ Cl 6-1126 Me₂NCl Cl SO₂Me 6-1127 Me₂N Cl pyrazol-1-yl SO₂Me 6-1128 Me₂N Cl 4-methoxy-SO₂Me pyrazol-1-yl 6-1129 Me₂N Cl 1,2,3-triazol-1-yl SO₂Me 6-1130 Me₂NCl 1,2,3-triazol-2-yl SO₂Me 6-1131 Me₂N Cl F SO₂Me 6-1132 Me₂N Me SO₂MeSO₂Me 6-1133 Me₂N Me SO₂Me CF₃ 6-1134 Me₂N Me NMe₂ SO₂Me 6-1135 Me₂N MeS(O)Me CF₃ 6-1136 Me₂N Me SMe CF₃ 6-1137 Me₂N Me SO₂CH₂CH₂OMe CF₃ 6-1138Me₂N Me pyrazol-1-yl SO₂Me 6-1139 Me₂N Me 4-methoxy- SO₂Me pyrazol-1-yl6-1140 Me₂N Me 1,2,3-triazol-1-yl SO₂Me 6-1141 Me₂N Me1,2,3-triazol-2-yl SO₂Me 6-1142 Me₂N Me Cl SO₂Me 6-1143 Me₂N Me Me SO₂Me6-1144 Me₂N Me Me SMe 6-1145 Me₂N Me SO₂Me Cl 6-1146 Me₂N Me NMe₂ SO₂Me6-1147 Me₂N Me NH(CH₂)₂OMe SO₂Me 6-1148 Me₂N CF₃ F SO₂CH₃ 6-1149 Me₂NCF₃ SMe SO₂CH₃ 6-1150 Me₂N CF₃ SEt SO₂CH₃ 6-1151 Me₂N CF₃ S(O)Et SO₂CH₃6-1152 Me₂N CF₃ SO₂CH₃ SO₂CH₃ 6-1153 Me₂N CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1154Me₂N CF₃ OCH₂(CO)NMe₂ SO₂Me 6-1155 Me₂N CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1156 Me₂N SMe SMe F 6-1157 Me₂N SMe SEt F 6-1158 Me₂N SO₂CH₃ F Cl6-1159 Me₂N F S(O)Me CF₃ 6-1160 Me₂N F SMe CF₃ 6-1161 Ph—NH NO₂ H SO₂Me6-1162 Ph—NH Cl H SO₂Me 6-1163 Ph—NH SO₂Me H CF₃ 6-1164 Ph—NH NO₂ H OMe6-1165 Ph—NH NO₂ H Br 6-1166 Ph—NH NO₂ H CF₃ 6-1167 Ph—NH NO₂ H NO₂6-1168 Ph—NH NO₂ H Cl 6-1169 Ph—NH NO₂ H Me 6-1170 Ph—NH NO₂ H F 6-1171Ph—NH OMe H SO₂Me 6-1172 Ph—NH CF₃ H NO₂ 6-1173 Ph—NH CH₂SO₂Me H Br6-1174 Ph—NH Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 9.58 (bs, 1H),8.04 (d, 1H), 7.55 (d, 1H), 5.22 (s, 2H), 4.25 (q, 2H), 2.67 (s, 3H)6-1175 Ph—NH Cl CH₂OCH₂CF₃ SMe 6-1176 Ph—NH Cl 5-cyanomethyl- SO₂Et4,5-dihydro-1,2- oxazol-3-yl 6-1177 Ph—NH Cl 4,5-dihydro-1,2- SO₂Etoxazol-3-yl 6-1178 Ph—NH Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-1179Ph—NH Cl SMe Cl 6-1180 Ph—NH Cl SMe SO₂Me 6-1181 Ph—NH Cl Me SO₂Et6-1182 Ph—NH Cl O(CH₂)₂OMe Cl 6-1183 Ph—NH Cl OCH₂- Cl cyclopropyl6-1184 Ph—NH Cl OMe Cl 6-1185 Ph—NH Cl NHAc Cl 6-1186 Ph—NH ClOCH₂C(O)NMe₂ Cl 6-1187 Ph—NH Cl Cl SO₂Me 6-1188 Ph—NH Cl pyrazol-1-ylSO₂Me 6-1189 Ph—NH Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1190 Ph—NH Cl1,2,3-triazol-1-yl SO₂Me 6-1191 Ph—NH Cl 1,2,3-triazol-2-yl SO₂Me 6-1192Ph—NH Cl F SO₂Me 6-1193 Ph—NH Me SO₂Me SO₂Me 6-1194 Ph—NH Me SO₂Me CF₃6-1195 Ph—NH Me NMe₂ SO₂Me 6-1196 Ph—NH Me S(O)Me CF₃ 6-1197 Ph—NH MeSMe CF₃ 6-1198 Ph—NH Me SO₂CH₂CH₂OMe CF₃ 6-1199 Ph—NH Me pyrazol-1-ylSO₂Me 6-1200 Ph—NH Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1201 Ph—NH Me1,2,3-triazol-1-yl SO₂Me 6-1202 Ph—NH Me 1,2,3-triazol-2-yl SO₂Me 6-1203Ph—NH Me Cl SO₂Me 6-1204 Ph—NH Me Me SO₂Me 6-1205 Ph—NH Me Me SMe 6-1206Ph—NH Me SO₂Me Cl 6-1207 Ph—NH Me NMe₂ SO₂Me 6-1208 Ph—NH Me NH(CH₂)₂OMeSO₂Me 6-1209 Ph—NH CF₃ F SO₂CH₃ 6-1210 Ph—NH CF₃ SMe SO₂CH₃ 6-1211 Ph—NHCF₃ SEt SO₂CH₃ 6-1212 Ph—NH CF₃ S(O)Et SO₂CH₃ 6-1213 Ph—NH CF₃ SO₂CH₃SO₂CH₃ 6-1214 Ph—NH CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1215 Ph—NH CF₃ OCH₂(CO)NMe₂SO2Me 6-1216 Ph—NH CF₃ CH₂O- SO₂Et tetrahydrofuran- 2-yl 6-1217 Ph—NHSMe SMe F 6-1218 Ph—NH SMe SEt F 6-1219 Ph—NH SO₂CH₃ F Cl 6-1220 Ph—NH FS(O)Me CF₃ 6-1221 Ph—NH F SMe CF₃ 6-1222 morpholin-1-yl NO₂ H SO₂Me6-1223 morpholin-1-yl Cl H SO₂Me 6-1224 morpholin-1-yl SO₂Me H CF₃6-1225 morpholin-1-yl NO₂ H OMe 6-1226 morpholin-1-yl NO₂ H Br 6-1227morpholin-1-yl NO₂ H CF₃ 6-1228 morpholin-1-yl NO₂ H NO₂ 6-1229morpholin-1-yl NO₂ H Cl 6-1230 morpholin-1-yl NO₂ H Me 6-1231morpholin-1-yl NO₂ H F 6-1232 morpholin-1-yl OMe H SO₂Me 6-1233morpholin-1-yl CF₃ H NO₂ 6-1234 morpholin-1-yl CH₂SO₂Me H Br 6-1235morpholin-1-yl Cl CH₂OCH₂CF₃ SO₂Me ¹H NMR, DMSO-d₆, 400 MHz 9.58 (bs,1H), 8.04 (d, 1H), 7.55 (d, 1H), 5.22 (s, 2H), 4.26 (q, 2H), 3.70-2.94(m, 11H) 6-1236 morpholin-1-yl Cl CH₂OCH₂CF₃ SMe 6-1237 morpholin-1-ylCl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 6-1238morpholin-1-yl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-1239morpholin-1-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-1240morpholin-1-yl Cl SMe Cl 6-1241 morpholin-1-yl Cl SMe SO₂Me 6-1242morpholin-1-yl Cl Me SO₂Et 6-1243 morpholin-1-yl Cl O(CH₂)₂OMe Cl 6-1244morpholin-1-yl Cl OCH₂- Cl cyclopropyl 6-1245 morpholin-1-yl Cl OMe Cl6-1246 morpholin-1-yl Cl NHAc Cl 6-1247 morpholin-1-yl Cl OCH₂C(O)NMe₂Cl 6-1248 morpholin-1-yl Cl Cl SO₂Me 6-1249 morpholin-1-yl Clpyrazol-1-yl SO₂Me 6-1250 morpholin-1-yl Cl 4-methoxy- SO₂Mepyrazol-1-yl 6-1251 morpholin-1-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-1252morpholin-1-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-1253 morpholin-1-yl Cl FSO₂Me 6-1254 morpholin-1-yl Me SO₂Me SO₂Me 6-1255 morpholin-1-yl MeSO₂Me CF₃ 6-1256 morpholin-1-yl Me NMe₂ SO₂Me 6-1257 morpholin-1-yl MeS(O)Me CF₃ 6-1258 morpholin-1-yl Me SMe CF₃ 6-1259 morpholin-1-yl MeSO₂CH₂CH₂OMe CF₃ 6-1260 morpholin-1-yl Me pyrazol-1-yl SO₂Me 6-1261morpholin-1-yl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1262 morpholin-1-yl Me1,2,3-triazol-1-yl SO₂Me 6-1263 morpholin-1-yl Me 1,2,3-triazol-2-ylSO₂Me 6-1264 morpholin-1-yl Me Cl SO₂Me 6-1265 morpholin-1-yl Me MeSO₂Me 6-1266 morpholin-1-yl Me Me SMe 6-1267 morpholin-1-yl Me SO₂Me Cl6-1268 morpholin-1-yl Me NMe₂ SO₂Me 6-1269 morpholin-1-yl Me NH(CH₂)₂OMeSO₂Me 6-1270 morpholin-1-yl CF₃ F SO₂CH₃ 6-1271 morpholin-1-yl CF₃ SMeSO₂CH₃ 6-1272 morpholin-1-yl CF₃ SEt SO₂CH₃ 6-1273 morpholin-1-yl CF₃S(O)Et SO₂CH₃ 6-1274 morpholin-1-yl CF₃ SO₂CH₃ SO₂CH₃ 6-1275morpholin-1-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1276 morpholin-1-yl CF₃OCH₂(CO)NMe₂ SO2Me 6-1277 morpholin-1-yl CF₃ CH₂O- SO₂Ettetrahydrofuran- 2-yl 6-1278 morpholin-1-yl SMe SMe F 6-1279morpholin-1-yl SMe SEt F 6-1280 morpholin-1-yl SO₂CH₃ F Cl 6-1281morpholin-1-yl F S(O)Me CF₃ 6-1282 morpholin-1-yl F SMe CF₃ 6-1283sec-Bu NO₂ H SO₂Me 6-1284 sec-Bu Cl H SO₂Me 6-1285 sec-Bu SO₂Me H CF₃6-1286 sec-Bu NO₂ H OMe 6-1287 sec-Bu NO₂ H Br 6-1288 sec-Bu NO₂ H CF₃6-1289 sec-Bu NO₂ H NO₂ 6-1290 sec-Bu NO₂ H Cl 6-1291 sec-Bu NO₂ H Me6-1292 sec-Bu NO₂ H F 6-1293 sec-Bu OMe H SO₂Me 6-1294 sec-Bu CF₃ H NO₂6-1295 sec-Bu CH₂SO₂Me H Br 6-1296 sec-Bu Cl CH₂OCH₂CF₃ SO₂Me 6-1297sec-Bu Cl CH₂OCH₂CF₃ SMe 6-1298 sec-Bu Cl 5-cyanomethyl- SO₂Et4,5-dihydro-1,2- oxazol-3-yl 6-1299 sec-Bu Cl 4,5-dihydro-1,2- SO₂Etoxazol-3-yl 6-1300 sec-Bu Cl CH₂OCH₂- SO₂Me tetrahydrofuran- 2-yl 6-1301sec-Bu Cl SMe Cl 6-1302 sec-Bu Cl SMe SO₂Me 6-1303 sec-Bu Cl Me SO₂Et6-1304 sec-Bu Cl O(CH₂)₂OMe Cl 6-1305 sec-Bu Cl OCH₂- Cl cyclopropyl6-1306 sec-Bu Cl OMe Cl 6-1307 sec-Bu Cl NHAc Cl 6-1308 sec-Bu ClOCH₂C(O)NMe₂ Cl 6-1309 sec-Bu Cl Cl SO₂Me 6-1310 sec-Bu Cl pyrazol-1-ylSO₂Me 6-1311 sec-Bu Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1312 sec-Bu Cl1,2,3-triazol-1-yl SO₂Me 6-1313 sec-Bu Cl 1,2,3-triazol-2-yl SO₂Me6-1314 sec-Bu Cl F SO₂Me 6-1315 sec-Bu Me SO₂Me SO₂Me 6-1316 sec-Bu MeSO₂Me CF₃ 6-1317 sec-Bu Me NMe₂ SO₂Me 6-1318 sec-Bu Me S(O)Me CF₃ 6-1319sec-Bu Me SMe CF₃ 6-1320 sec-Bu Me SO₂CH₂CH₂OMe CF₃ 6-1321 sec-Bu Mepyrazol-1-yl SO₂Me 6-1322 sec-Bu Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1323sec-Bu Me 1,2,3-triazol-1-yl SO₂Me 6-1324 sec-Bu Me 1,2,3-triazol-2-ylSO₂Me 6-1325 sec-Bu Me Cl SO₂Me 6-1326 sec-Bu Me Me SO₂Me 6-1327 sec-BuMe Me SMe 6-1328 sec-Bu Me SO₂Me Cl 6-1329 sec-Bu Me NMe₂ SO₂Me 6-1330sec-Bu Me NH(CH₂)₂OMe SO₂Me 6-1331 sec-Bu CF₃ F SO₂CH₃ 6-1332 sec-Bu CF₃SMe SO₂CH₃ 6-1333 sec-Bu CF₃ SEt SO₂CH₃ 6-1334 sec-Bu CF₃ S(O)Et SO₂CH₃6-1335 sec-Bu CF₃ SO₂CH₃ SO₂CH₃ 6-1336 sec-Bu CF₃ OCH₂CH₂OMe SO₂CH₃6-1337 sec-Bu CF₃ OCH₂(CO)NMe₂ SO2Me 6-1338 sec-Bu CF₃ CH₂O- SO₂Ettetrahydrofuran- 2-yl 6-1339 sec-Bu SMe SMe F 6-1340 sec-Bu SMe SEt F6-1341 sec-Bu SO₂CH₃ F Cl 6-1342 sec-Bu F S(O)Me CF₃ 6-1343 sec-Bu F SMeCF₃

TABLE 7 Inventive compounds of the general formula (I) in which A isnitrogen

Physical data No. R X Z (¹H NMR, DMSO-d₆, 400 MHz) 7-1 H Cl CF₃ 7-2 MeCl CF₃ 12.59 (bs, 1H), 8.48 (d, 1H), 8.12 (d, 1H) 7-3 Et Cl CF₃ ¹H NMR,DMSO-d₆, 400 MHz 12.59 (bs, 1H), 8.49 (d, 1H), 8.11 (d, 1H), 2.85 (q,2H), 1.28 (t, 3H) 7-4 CF₃ Cl CF₃ 7-5 CH₂OMe Cl CF₃ 7-6 c-Pr Cl CF₃ 7-7CO₂Et Cl CF₃ 13.14 (bs, 1H), 8.50 (d, 1H), 8.17 (d, 1H), 4.42 (q, 2H),1.33 (t, 3H) 7-8 CO₂Me Cl CF₃ 7-9 benzyl Cl CF₃ 8.46 (d, 1H), 8.10 (d,1H), 7.41- 7.28 (m, 3H), 7.17 (bs, 2H), 4.25 (s, 2H) 7-10 phenyl Cl CF₃12.88 (bs, 1H), 8.51 (d, 1H), 8.17 (d, 1H), 7.94 (bs, 2H), 7.67-7.57 (m,3H) 7-11 pyrazin-2-yl Cl CF₃ 13.10 (bs, 1H), 9.36 (s, 1H), 8.88 (m, 2H),8.54 (d, 1H), 8.17 (d, 1H) 7-12 4-OMe—Ph Cl CF₃ 12.78 (bs, 1H), 8.51 (d,1H), 8.16 (d, 1H), 7.38 (d, 2H), 7.17 (d, 2H), 3.84 (s, 3H) 7-13 4-Cl—PhCl CF₃ 12.90 (bs, 1H), 8.51 (d, 1H), 8.18 (d, 1H), 7.94 (d, 2H), 7.69(d, 2H) 7-14 t-Bu Cl CF₃ 12.60 (bs, 1H), 8.48 (d, 1H), 8.12 (d, 1H),1.32 (bs, 9H) 7-15 furan-2-yl Cl CF₃ 12.83 (bs, 1H), 8.51 (d, 1H), 8.17(d, 1H), 8.06 (s, 1H), 7.29 (s, 1H), 6.80 (m, 1H) 7-16 i-Pr Cl CF₃ 12.26(bs, 1H), 8.31 (d, 1H), 8.02 (d, 1H), 4.72 (s, 2H), 3.25 (s, 3H), 3.19(m, 1H), 1.30 (d, 6H) 7-17 CH₂CH₂OMe Cl CF₃ 12.61 (bs, 1H), 8.48 (d,1H), 8.12 (d, 1H), 3.69 (t, 2H), 3.09 (t, 2H) 7-18 CH₂CF₃ Cl CF₃ 12.82(bs, 1H), 8.50 (d, 1H), 8.16 (d, 1H), 4.33 (q, 2H) 7-19tetrahydrofuran-2-yl Cl CF₃ 12.73 (bs, 1H), 8.48 (d, 1H), 8.15 (d, 1H),5.11 (t, 1H), 3.84 (t, 2H), 2.31-2.18 (m, 2H), 2.0 (q, 2H) 7-20 n-Pr ClCF₃ 12.61 (bs, 1H), 8.48 (d, 1H), 8.12 (d, 1H), 2.81 (t, 2H), 1.71 (q,2H), 0.96 (t, 3H) 7-21 CH₂OEt Cl CF₃ 7-22 cyclobutyl Cl CF₃ 12.62 (bs,1H), 8.47 (d, 1H), 8.13 (d, 1H), 3.76-3.72 (m, 1H), 2.41- 2.22 (m, 4H)7-23 cyclopentyl Cl CF₃ 12.65 (bs, 1H), 8.47 (d, 1H), 8.13 (d, 1H), 3.32(m, 1H), 2.18-1.97 (m, 2H), 1.83-1.73 (m, 2H), 1.71- 1.61 (m, 6H) 7-24Me₂N Cl CF₃ 7-25 Ph—NH Cl CF₃ 7-26 morpholin-1-yl Cl CF₃ 8.59 (d, 1H),8.17 (d, 1H), 3.67 (m, 4H), 3.60 (m, 4H) 7-27 H Cl Cl 7-28 Me Cl Cl 7-29Et Cl Cl 7-30 CF₃ Cl Cl 13.21 (s, 1H), 8.23 (d, 1H), 7.78 (d, 1H) 7-31CH₂OMe Cl Cl 7-32 c-Pr Cl Cl 7-33 CO₂Et Cl Cl 7-34 CO₂Me Cl Cl 7-35benzyl Cl Cl 7-36 phenyl Cl Cl 7-37 pyrazin-2-yl Cl Cl 7-38 4-OMe—Ph ClCl 7-39 4-Cl—Ph Cl Cl 7-40 t-Bu Cl Cl 7-41 furan-2-yl Cl Cl 7-42 i-Pr ClCl 7-43 CH₂CH₂OMe Cl Cl 7-44 CH₂CF₃ Cl Cl 7-45 tetrahydrofuran-2-yl ClCl 7-46 n-Pr Cl Cl 7-47 CH₂OEt Cl Cl 7-48 cyclobutyl Cl Cl 7-49cyclopentyl Cl Cl 7-50 Me₂N Cl Cl 7-51 Ph—NH Cl Cl 7-52 morpholin-1-ylCl Cl 7-53 H Me Cl 7-54 Me Me Cl 7-55 Et Me Cl 11.43 (s, 1H), 8.04 (d,1H), 4.45 (d, 1H), 2.81 (q, 2H), 2.54 (s, 3H), 1.27 (t, 3H) 7-56 CF₃ MeCl 7-57 CH₂OMe Me Cl 7-58 c-Pr Me Cl 7-59 CO₂Et Me Cl 7-60 CO₂Me Me Cl7-61 benzyl Me Cl 7-62 phenyl Me Cl 7-63 pyrazin-2-yl Me Cl 7-644-OMe—Ph Me Cl 7-65 4-Cl—Ph Me Cl 7-66 t-Bu Me Cl 7-67 furan-2-yl Me Cl7-68 i-Pr Me Cl 7-69 CH₂CH₂OMe Me Cl 7-70 CH₂CF₃ Me Cl 7-71tetrahydrofuran-2-yl Me Cl 7-72 n-Pr Me Cl 7-73 CH₂OEt Me Cl 7-74cyclobutyl Me Cl 7-75 cyclopentyl Me Cl 7-76 Me₂N Me Cl 7-77 Ph—NH Me Cl7-78 morpholin-1-yl Me Cl 7-79 H Cl SMe 7-80 Me Cl SMe 7-81 Et Cl SMe7-82 CF₃ Cl SMe 7-83 CH₂OMe Cl SMe 7-84 c-Pr Cl SMe 7-85 CO₂Et Cl SMe7-86 CO₂Me Cl SMe 7-87 benzyl Cl SMe 7-88 phenyl Cl SMe 7-89pyrazin-2-yl Cl SMe 7-90 4-OMe—Ph Cl SMe 7-91 4-Cl—Ph Cl SMe 7-92 t-BuCl SMe 7-93 furan-2-yl Cl SMe 7-94 i-Pr Cl SMe 7-95 CH₂CH₂OMe Cl SMe7-96 CH₂CF₃ Cl SMe 7-97 tetrahydrofuran-2-yl Cl SMe 7-98 n-Pr Cl SMe7-99 CH₂OEt Cl SMe 7-100 cyclobutyl Cl SMe 7-101 cyclopentyl Cl SMe7-102 Me₂N Cl SMe 7-103 Ph—NH Cl SMe 7-104 morpholin-1-yl Cl SMe 7-105 HCl SO₂Me 7-106 Me Cl SO₂Me 7-107 Et Cl SO₂Me 7-108 CF₃ Cl SO₂Me 7-109CH₂OMe Cl SO₂Me 7-110 c-Pr Cl SO₂Me 7-111 CO₂Et Cl SO₂Me 7-112 CO₂Me ClSO₂Me 7-113 benzyl Cl SO₂Me 7-114 phenyl Cl SO₂Me 7-115 pyrazin-2-yl ClSO₂Me 7-116 4-OMe—Ph Cl SO₂Me 7-117 4-Cl—Ph Cl SO₂Me 7-118 t-Bu Cl SO₂Me7-119 furan-2-yl Cl SO₂Me 7-120 i-Pr Cl SO₂Me 7-121 CH₂CH₂OMe Cl SO₂Me7-122 CH₂CF₃ Cl SO₂Me 7-123 tetrahydrofuran-2-yl Cl SO₂Me 7-124 n-Pr ClSO₂Me 7-125 CH₂OEt Cl SO₂Me 7-126 cyclobutyl Cl SO₂Me 7-127 cyclopentylCl SO₂Me 7-128 Me₂N Cl SO₂Me 7-129 Ph—NH Cl SO₂Me 7-130 morpholin-1-ylCl SO₂Me 7-131 H Me CF₃ 7-132 Me Me CF₃ 7-133 Et Me CF₃ 7-134 CF₃ Me CF₃13.06 (bs, 1H), 8.26 (d, 1H), 7.92 (d, 1H), 2.67 (s, 3H) 7-135 CH₂OMe MeCF₃ 7-136 c-Pr Me CF₃ 12.30 (bs, 1H), 8.26 (d, 1H), 7.87 (d, 1H), 2.63(s, 3H), 2.19 (m, 1H), 1.10 (m, 2H), 0.96 (m, 2H) 7-137 CO₂Et Me CF₃7-138 CO₂Me Me CF₃ 7-139 benzyl Me CF₃ 7-140 phenyl Me CF₃ 7-141pyrazin-2-yl Me CF₃ 7-142 4-OMe—Ph Me CF₃ 12.50 (bs, 1H), 8.30 (d, 1H),7.90 (d, 1H), 7.89 (d, 2H), 7.17 (d, 2H), 3.86 (s, 3H), 2.69 (s, 3H)7-143 4-Cl—Ph Me CF₃ 7-144 t-Bu Me CF₃ 12.29 (bs, 1H), 8.28 (d, 1H),7.87 (d, 1H), 2.66 (s, 3H). 1.35 (s, 9H) 7-145 furan-2-yl Me CF₃ 7-146i-Pr Me CF₃ 12.33 (bs, 1H), 8.26 (d, 1H), 7.88 (d, 1H), 3.17 (m, 1H),2.66 (s, 3H), 1.30 (d, 6H) 7-147 CH₂CH₂OMe Me CF₃ 7-148 CH₂CF₃ Me CF₃7-149 tetrahydrofuran-2-yl Me CF₃ 7-150 n-Pr Me CF₃ 12.30 (bs, 1H), 8.26(d, 1H), 7.88 (d, 1H), 2.81 (s, 2H), 2.65 (s, 3H), 1.71 (m, 2H), 0.97(t, 3H) 7-151 CH₂OEt Me CF₃ 7-152 cyclobutyl Me CF₃ 12.32 (bs, 1H), 8.26(d, 1H), 7.89 (d, 1H), 3.76-3.70 (m, 1H), 2.66 (s, 3H), 2.41-2.22 (m,4H), 2.12-2.00 (m, 1H), 1.98-1.91 (m, 1H) 7-153 cyclopentyl Me CF₃ 12.28(bs, 1H), 8.30 (d, 1H), 7.87 (d, 1H), 3.37 (m, 1H), 2.65 (s, 3H),2.09-1.98 (m, 2H), 1.88-1.76 (m, 2H), 1.75-1.69 (m, 4H) 7-154 Me₂N MeCF₃ 7-155 Ph—NH Me CF₃ 10.81 (s, 1H), 8.41 (d, 1H), 7.96 (d, 1H), 7.64(d, 2H), 7.39 (dd, 2H), 7.05 (dd, 1H), 2.93 (s, 3H) 7-156 morpholin-1-ylMe CF₃ 7-157 H CH₂OMe CF₃ 7-158 Me CH₂OMe CF₃ 12.26 (bs, 1H), 8.30 (d,1H), 8.02 (d, 1H), 4.71 (s, 2H), 3.25 (s, 3H) 7-159 Et CH₂OMe CF₃ 12.28(bs, 1H), 8.31 (d, 1H), 8.02 (d, 1H), 4.72 (s, 2H), 3.25 (s, 3H), 2.86(q, 2H), 1.26 (t, 3H) 7-160 CF₃ CH₂OMe CF₃ 13.03 (bs, 1H), 8.32 (d, 1H),8.06 (d, 1H), 4.72 (s, 2H), 3.25 (s, 3H) 7-161 CH₂OMe CH₂OMe CF₃ 12.41(bs, 1H), 8.32 (d, 1H), 8.03 (d, 1H), 4.72 (s, 2H), 4.63 (s, 2H), 3.36(s, 3H), 3.25 (s, 3H) 7-162 c-Pr CH₂OMe CF₃ 7-163 CO₂Et CH₂OMe CF₃ 7-164CO₂Me CH₂OMe CF₃ 7-165 benzyl CH₂OMe CF₃ 7-166 phenyl CH₂OMe CF₃ 7-167pyrazin-2-yl CH₂OMe CF₃ 7-168 4-OMe—Ph CH₂OMe CF₃ 7-169 4-Cl—Ph CH₂OMeCF₃ 7-170 t-Bu CH₂OMe CF₃ 7-171 furan-2-yl CH₂OMe CF₃ 7-172 i-Pr CH₂OMeCF₃ 12.26 (s, 1H), 8.31 (d, 1H), 8.02 (d, 1H), 4.72 (s, 2H), 3.23 (s,3H), 3.18 (m, 1H), 1.29 (d, 6H) 7-173 CH₂CH₂OMe CH₂OMe CF₃ 12.28 (s,1H), 8.31 (d, 1H), 8.02 (d, 1H), 5.07 (dd, 2H), 4.71 (s, 2H), 3.70 (t,2H), 3.25 (2s, 6H), 3.07 (t, 2H) 7-174 CH₂CF₃ CH₂OMe CF₃ 7-175tetrahydrofuran-2-yl CH₂OMe CF₃ 12.41 (s, 1H), 8.31 (d, 1H), 8.02 (d,1H), 5.11 (dd, 1H), 4.71 (s, 2H), 3.84 (t, 2H), 3.42 (s, 3H), 2.32-2.14(m, 2H), 2.06-1.90 (m, 2H) 7-176 n-Pr CH₂OMe CF₃ 12.22 (s, 1H), 8.31 (d,1H), 8.01 (d, 1H), 4.70 (s, 2H), 3.23 (s, 3H), 2.80 (t, 2H), 1.60 (m,2H), 0.94 (t, 3H) 7-177 CH₂OEt CH₂OMe CF₃ 7-178 cyclobutyl CH₂OMe CF₃12.26 (s, 1H), 8.31 (d, 1H), 8.01 (d, 1H), 4.72 (s, 2H), 3.78-3.70 (m,1H), 3.23 (s, 3H), 2.40-2.22 (m, 4H), 2.10-1.88 (m, 1H), 1.97- 1.88 (m,1H) 7-179 cyclopentyl CH₂OMe CF₃ 12.32 (s, 1H), 8.31 (d, 1H), 8.01 (d,1H), 4.71 (s, 2H), 3.25 (s, 3H), 2.09-1.98 (m, 2H), 1.88-1.60 (m, 6H)7-180 Me₂N CH₂OMe CF₃ 7-181 Ph—NH CH₂OMe CF₃ 7-182 morpholin-1-yl CH₂OMeCF₃ 7-183 H CH₂SMe CF₃ 7-184 Me CH₂SMe CF₃ 7-185 Et CH₂SMe CF₃ 7-186 CF₃CH₂SMe CF₃ 7-187 CH₂OMe CH₂SMe CF₃ 7-188 c-Pr CH₂SMe CF₃ 7-189 CO₂EtCH₂SMe CF₃ 7-190 CO₂Me CH₂SMe CF₃ 7-191 benzyl CH₂SMe CF₃ 7-192 phenylCH₂SMe CF₃ 7-193 pyrazin-2-yl CH₂SMe CF₃ 7-194 4-OMe—Ph CH₂SMe CF₃ 7-1954-Cl—Ph CH₂SMe CF₃ 7-196 t-Bu CH₂SMe CF₃ 7-197 furan-2-yl CH₂SMe CF₃7-198 i-Pr CH₂SMe CF₃ 7-199 CH₂CH₂OMe CH₂SMe CF₃ 7-200 CH₂CF₃ CH₂SMe CF₃7-201 tetrahydrofuran-2-yl CH₂SMe CF₃ 7-202 n-Pr CH₂SMe CF₃ 7-203 CH₂OEtCH₂SMe CF₃ 7-204 cyclobutyl CH₂SMe CF₃ 7-205 cyclopentyl CH₂SMe CF₃7-206 Me₂N CH₂SMe CF₃ 7-207 Ph—NH CH₂SMe CF₃ 7-208 morpholin-1-yl CH₂SMeCF₃ 7-209 H CH₂SO₂Me CF₃ 7-210 Me CH₂SO₂Me CF₃ 7-211 Et CH₂SO₂Me CF₃7-212 CF₃ CH₂SO₂Me CF₃ 7-213 CH₂OMe CH₂SO₂Me CF₃ 7-214 c-Pr CH₂SO₂Me CF₃7-215 CO₂Et CH₂SO₂Me CF₃ 7-216 CO₂Me CH₂SO₂Me CF₃ 7-217 benzyl CH₂SO₂MeCF₃ 7-218 phenyl CH₂SO₂Me CF₃ 7-219 pyrazin-2-yl CH₂SO₂Me CF₃ 7-2204-OMe—Ph CH₂SO₂Me CF₃ 7-221 4-Cl—Ph CH₂SO₂Me CF₃ 7-222 t-Bu CH₂SO₂Me CF₃7-223 furan-2-yl CH₂SO₂Me CF₃ 7-224 i-Pr CH₂SO₂Me CF₃ 7-225 CH₂CH₂OMeCH₂SO₂Me CF₃ 7-226 CH₂CF₃ CH₂SO₂Me CF₃ 7-227 tetrahydro- CH₂SO₂Me CF₃furan-2-yl 7-228 n-Pr CH₂SO₂Me CF₃ 7-229 CH₂OEt CH₂SO₂Me CF₃ 7-230cyclobutyl CH₂SO₂Me CF₃ 7-231 cyclopentyl CH₂SO₂Me CF₃ 7-232 Me₂NCH₂SO₂Me CF₃ 7-233 Ph—NH CH₂SO₂Me CF₃ 7-234 morpholin-1-yl CH₂SO₂Me CF₃7-235 H CH₂OC₂H₄OMe CF₃ 7-236 Me CH₂OC₂H₄OMe CF₃ 7-237 Et CH₂OC₂H₄OMeCF₃ 7-238 CF₃ CH₂OC₂H₄OMe CF₃ 7-239 CH₂OMe CH₂OC₂H₄OMe CF₃ 7-240 c-PrCH₂OC₂H₄OMe CF₃ 7-241 CO₂Et CH₂OC₂H₄OMe CF₃ 7-242 CO₂Me CH₂OC₂H₄OMe CF₃7-243 benzyl CH₂OC₂H₄OMe CF₃ 7-244 phenyl CH₂OC₂H₄OMe CF₃ 7-245pyrazin-2-yl CH₂OC₂H₄OMe CF₃ 7-246 4-OMe—Ph CH₂OC₂H₄OMe CF₃ 7-2474-Cl—Ph CH₂OC₂H₄OMe CF₃ 7-248 t-Bu CH₂OC₂H₄OMe CF₃ 7-249 furan-2-ylCH₂OC₂H₄OMe CF₃ 7-250 i-Pr CH₂OC₂H₄OMe CF₃ 7-251 CH₂CH₂OMe CH₂OC₂H₄OMeCF₃ 7-252 CH₂CF₃ CH₂OC₂H₄OMe CF₃ 7-253 tetrahydro- CH₂OC₂H₄OMe CF₃furan-2-yl 7-254 n-Pr CH₂OC₂H₄OMe CF₃ 7-255 CH₂OEt CH₂OC₂H₄OMe CF₃ 7-256cyclobutyl CH₂OC₂H₄OMe CF₃ 7-257 cyclopentyl CH₂OC₂H₄OMe CF₃ 7-258 Me₂NCH₂OC₂H₄OMe CF₃ 7-259 Ph—NH CH₂OC₂H₄OMe CF₃ 7-260 morpholin-1-ylCH₂OC₂H₄OMe CF₃ 7-261 H OCH₂- CF₃ tetrahydro- furan-2-yl 7-262 Me OCH₂-CF₃ tetrahydro- furan-2-yl 7-263 Et OCH₂- CF₃ tetrahydro- furan-2-yl7-264 CF₃ OCH₂- CF₃ tetrahydro- furan-2-yl 7-265 CH₂OMe OCH₂- CF₃tetrahydro- furan-2-yl 7-266 c-Pr OCH₂- CF₃ tetrahydro- furan-2-yl 7-267CO₂Et OCH₂- CF₃ tetrahydro- furan-2-yl 7-268 CO₂Me OCH₂- CF₃ tetrahydro-furan-2-yl 7-269 benzyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-270 phenylOCH₂- CF₃ tetrahydro- furan-2-yl 7-271 pyrazin-2-yl OCH₂- CF₃tetrahydro- furan-2-yl 7-272 4-OMe—Ph OCH₂- CF₃ tetrahydro- furan-2-yl7-273 4-Cl—Ph OCH₂- CF₃ tetrahydro- furan-2-yl 7-274 t-Bu OCH₂- CF₃tetrahydro- furan-2-yl 7-275 furan-2-yl OCH₂- CF₃ tetrahydro- furan-2-yl7-276 i-Pr OCH₂- CF₃ tetrahydro- furan-2-yl 7-277 CH₂CH₂OMe OCH₂- CF₃tetrahydro- furan-2-yl 7-278 CH₂CF₃ OCH₂- CF₃ tetrahydro- furan-2-yl7-279 tetrahydro- OCH₂- CF₃ furan-2-yl tetrahydro- furan-2-yl 7-280 n-PrOCH₂- CF₃ tetrahydro- furan-2-yl 7-281 CH₂OEt OCH₂- CF₃ tetrahydro-furan-2-yl 7-282 cyclobutyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-283cyclopentyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-284 Me₂N OCH₂- CF₃tetrahydro- furan-2-yl 7-285 Ph—NH OCH₂- CF₃ tetrahydro- furan-2-yl7-286 morpholin-1-yl OCH₂- CF₃ tetrahydro- furan-2-yl 7-287 H(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-288 Me(1,1-dioxido-1,2- CF₃ 8.32 (d, 1H), 8.02 (d, 1H), 4.50 (s,thiadiazolidin-1- 2H), 3.21 (m, 4H), 2.18 (m, 2H) yl)methyl 7-289 Et(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-290 CF₃(1,1-dioxido-1,2- CF₃ 8.32 (d, 1H), 8.06 (d, 1H), 4.48 (s,thiadiazolidin-1- 2H), 3.14 (m, 4H), 2.17 (m, 2H) yl)methyl 7-291 CH₂OMe(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-292 c-Pr(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-293 CO₂Et(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-294 CO₂Me(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-295 benzyl(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-296 phenyl(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-297 pyrazin-2-yl(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-298 4-OMe—Ph(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-299 4-Cl—Ph(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-300 t-Bu(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-301 furan-2-yl(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-302 i-Pr(1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-303 CH₂CH₂OMe(1,1-dioxido-1,2- CF₃ 12.34 (bs, 1H), 8.33 (d, 1H), 8.02thiadiazolidin-1- (d, 1H), 4.50 (s, 2H), 3.67 (t, 2H), yl)methyl 3.27(s, 3H), 3.21 (m, 4H), 3.09 (t, 2H), 2.18 (m, 2H) 7-304 CH₂CF₃(1,1-dioxido-1,2- CF₃ 12.59 (bs, 1H), 8.33 (d, 1H), 8.03thiadiazolidin-1- (d, 1H), 4.48 (s, 2H), 4.32 (q, 2H), yl)methyl 3.17(m, 4H), 2.17 (m, 2H) 7-305 tetrahydro- (1,1-dioxido-1,2- CF₃ furan-2-ylthiadiazolidin-1- yl)methyl 7-306 n-Pr (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-307 CH₂OEt (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-308 cyclobutyl (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-309 cyclopentyl (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-310 Me₂N (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-311 Ph—NH (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-312 morpholin-1-yl (1,1-dioxido-1,2- CF₃thiadiazolidin-1- yl)methyl 7-313 H (3-methyl-2- CF₃ oxoimidazolidin-1-yl)methyl 7-314 Me (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-315Et (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-316 CF₃ (3-methyl-2-CF₃ oxoimidazolidin- 1-yl)methyl 7-317 CH₂OMe (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-318 c-Pr (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-319 CO₂Et (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-320 CO₂Me (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-321 benzyl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-322 phenyl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-323 pyrazin-2-yl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-324 4-OMe—Ph (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-325 4-Cl—Ph (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-326 t-Bu (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-327 furan-2-yl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-328 i-Pr (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-329 CH₂CH₂OMe (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-330 CH₂CF₃ (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-331 tetrahydro- (3-methyl-2- CF₃furan-2-yl oxoimidazolidin- 1-yl)methyl 7-332 n-Pr (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-333 CH₂OEt (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-334 cyclobutyl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-335 cyclopentyl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-336 Me₂N (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-337 Ph—NH (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-338 morpholin-1-yl (3-methyl-2- CF₃oxoimidazolidin- 1-yl)methyl 7-339 H (3-methoxy-4- CF₃ methyl-5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-340 Me (3-methoxy-4- CF₃methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-341 Et(3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1-yl)methyl 7-342 CF₃ (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-343 CH₂OMe (3-methoxy-4- CF₃ methyl-5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-344 c-Pr (3-methoxy-4- CF₃methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-345 CO₂Et(3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1-yl)methyl 7-346 CO₂Me (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-347 benzyl (3-methoxy-4- CF₃ methyl-5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-348 phenyl (3-methoxy-4-CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-349pyrazin-2-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-350 4-OMe—Ph (3-methoxy-4- CF₃methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-351 4-Cl—Ph(3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1-yl)methyl 7-352 t-Bu (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-353 furan-2-yl (3-methoxy-4- CF₃methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-354 i-Pr(3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1-yl)methyl 7-355 CH₂CH₂OMe (3-methoxy-4- CF₃ methyl-5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-356 CH₂CF₃ (3-methoxy-4-CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-357tetrahydro- (3-methoxy-4- CF₃ furan-2-yl methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-358 n-Pr (3-methoxy-4- CF₃ methyl-5-oxo-4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-359 CH₂OEt (3-methoxy-4-CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-360cyclobutyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-361 cyclopentyl (3-methoxy-4- CF₃methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-362 Me₂N(3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1-yl)methyl 7-363 Ph—NH (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H-1,2,4-triazol-1- yl)methyl 7-364 morpholin-1-yl (3-methoxy-4- CF₃methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-365 i-Pr ClMe 11.36 (s, 1H), 8.03 (d, 1H), 7.45 (d, 1H), 3.25 (m, 1H), 1.31 (t, 3H)

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and/or salts thereof and 90 parts by    weight of talc as an inert substance, and comminuting the mixture in    a hammer mill.-   b) A readily water-dispersible wettable powder is obtained by mixing    25 parts by weight of a compound of the formula (I) and/or salts    thereof, 64 parts by weight of kaolin-containing quartz as an inert    substance, 10 parts by weight of potassium lignosulfonate and 1 part    by weight of sodium oleylmethyltaurate as a wetting agent and    dispersant, and grinding the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277° C.), and grinding the    mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as a solvent and 10 parts by weight of    ethoxylated nonylphenol as an emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium laurylsulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin, grinding the mixture in a        pinned-disk mill and granulating the powder in a fluidized bed        by spraying on water as a granulating liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleylmethyltaurate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water    -   in a colloid mill, then grinding the mixture in a bead mill and        atomizing and drying the resulting suspension in a spray tower        by means of a one-substance nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action AgainstHarmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in wood-fiber pots in sandy loam and covered with soil. Theinventive compounds formulated in the form of wettable powders (WP) oras emulsion concentrates (EC) are then applied to the surface of thecovering soil as an aqueous suspension or emulsion at a waterapplication rate of 600 to 8001/ha (converted) with addition of 0.2%wetting agent. After the treatment, the pots are placed in a greenhouseand kept under good growth conditions for the test plants. The damage tothe test plants is assessed visually after a test period of 3 weeks bycomparison with untreated controls (herbicidal activity in percent (%):100% action=the plants have died, 0% action=like control plants). Forexample, compounds No. 6-028, 6-767, 6-889 and 6-627 at an applicationrate of 320 g/ha each show at least 80% efficacy against Amaranthusretroflexus and Veronica persica. Compounds No. 3-264, 3-145, 4-145,4-144, 2-264 and 3-264 at an application rate of 320 g/ha each show atleast 80% efficacy against Abutilon theophrasti and Matricaria inodora.Compounds No. 6-645 and 2-255 at an application rate of 320 g/ha eachshow at least 80% efficacy against Setaria viridis and Viola tricolor.Compounds No. 6-705, 4-255 and 2-246 at an application rate of 320 g/haeach show at least 80% efficacy against Amaranthus retroflexus andMatricaria inodora.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Theinventive compounds formulated in the form of wettable powders (WP) oras emulsion concentrates (EC) are then sprayed onto the green parts ofthe plants as an aqueous suspension or emulsion at a water applicationrate of 600 to 8001/ha (converted) with addition of 0.2% wetting agent.After the test plants have been left to stand in the greenhouse underoptimal growth conditions for about 3 weeks, the action of theformulations is assessed visually in comparison to untreated controls(herbicidal action in percent (%): 100% action=the plants have died, 0%action=like control plants).

For example, compounds No. 7-3, 6-584, 6-645, 2-240, 2-246 and 3-264 atan application rate of 80 g/ha each show at least 80% efficacy againstEchinochloa crus galli and Pharbitis purpureum. Compounds No. 2-255,4-144, 2-246, 3-264 and 5-290 at an application rate of 80 g/ha eachshow at least 80% efficacy against Abutilon theophrasti and Amaranthusretroflexus. Compounds No. 4-145, 6-767, 6-889 and 2-264 at anapplication rate of 80 g/ha each show at least 80% efficacy againstViola tricolor. Compounds No. 4-255, 6-699, 6-028, 6-625 and 6-688 at anapplication rate of 80 g/ha each show at least 80% efficacy againstStellaria media.

1. An N-(1,3,4-oxadiazol-2-yl)arylcarboxamide of formula (I) and/or asalt thereof

in which the substituents are defined as follows: A is N or CY, R ishydrogen, (C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, CH₂R⁶, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR¹, NHR¹, methoxycarbonyl,ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino,methylsulfenyl, methylsulfinyl, methylsulfonyl, or heteroaryl,heterocyclyl, benzyl or phenyl each substituted by at least one sradical selected from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, X is nitro, halogen, cyano, formyl,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂,CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, wherethe two latter radicals are each substituted by s halogen,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy radicals, and where heterocyclylbears n oxo groups, Y is hydrogen, nitro, halogen, cyano, thiocyanato,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,CO(NOR¹)R¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylphenyl,(C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, phenyl, heteroarylor heterocyclyl, where the 6 latter radicals are each substituted by atleast one s radical selected from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylbears n oxo groups, Z is halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, heteroaryl, heterocyclyl orphenyl, where the three latter radicals are each substituted by at leastone s radical selected from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or halo-(C₁-C₆)-alkoxy, and whereheterocyclyl bears n oxo groups, or Z may also be hydrogen if Y is theS(O)_(n)R² radical, R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocycl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by at least one s radical selected from the group consistingof cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³,COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by at least one s radical selected from the group consistingof cyano, halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³,COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁵ is methyl orethyl, R⁶ is acetoxy, acetamido, N-methylacetamido, benzoyloxy,benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,dimethylaminocarbonyl, (C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, orheteroaryl, heterocyclyl or phenyl each substituted by at least one sradical selected from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen, n is 0, 1 or 2; s is 0, 1, 2 or 3, with theproviso that a) X and Z are not both the same radical from the group ofchlorine, fluorine, methoxy and methyl when Y is hydrogen, b) X is nothydroxyl when Y is hydrogen and Z is methoxy, c) X is not chlorine orbromine when Y is hydrogen and Z is fluorine, d) X is not fluorine whenY is hydrogen and Z is bromine, e) X or Z is not hydrogen when A isnitrogen, f) R is not trifluoromethyl when X is acetoxy and Z is methyl.2. An N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, inwhich A is N or CY, R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl, benzyl,pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine,dimethylamino, or phenyl substituted by at least one s radical selectedfrom the group consisting of methyl, methoxy, trifluoromethyl andhalogen; X is nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, where the two latter radicals are eachsubstituted by s halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy radicals,and where heterocyclyl bears n oxo groups, Y hydrogen, nitro, halogen,cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂,N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the6 latter radicals are each substituted by at least one s radicalselected from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylbears n oxo groups, Z is halogen, cyano, nitro, methyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)R², 1,2,4-triazol-1-yl,pyrazol-1-yl, or Z may also be hydrogen if Y is the S(O)_(n)R² radical,R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe 16 latter radicals are substituted by at least one s radicalselected from the group consisting of cyano, halogen, nitro, OR³,S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR^(S), OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³,CON(R³)₂ and (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and whereheterocyclyl bears n oxo groups, R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkylor (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where these three aforementionedradicals are each substituted by at least one s radical selected fromthe group consisting of halogen and OR³, R³ is hydrogen or(C₁-C₆)-alkyl, R⁴ is (C₁-C₆)-alkyl, n is 0, 1 or 2; s is 0, 1, 2 or 3,with the proviso that a) X and Z are not both the same radical from thegroup of chlorine, fluorine, methoxy and methyl when Y is hydrogen, b) Xis not hydroxyl when Y is hydrogen and Z is methoxy, c) X is notchlorine or bromine when Y is hydrogen and Z is fluorine, d) X is notfluorine when Y is hydrogen and Z is bromine, e) X or Z is not hydrogenwhen A is nitrogen, f) is not trifluoromethyl when X is acetoxy and Z ismethyl.
 3. A herbicidal composition, comprising a herbicidally activecontent of at least one compound of formula (I) and/or salt thereof asclaimed in claim
 1. 4. The herbicidal composition as claimed in claim 3,in a mixture with at least one formulation auxiliary.
 5. The herbicidalcomposition as claimed in claim 3, comprising at least one furtherpesticidally active substance selected from the group consisting of aninsecticide, an acaricide, a herbicide, a fungicide, a safener and agrowth regulator.
 6. The herbicidal composition as claimed in claim 5,comprising a safener.
 7. The herbicidal composition as claimed in claim6, comprising a cyprosulfamide, a cloquintocet-mexyl, a mefenpyr-diethyland/or an isoxadifen-ethyl.
 8. The herbicidal composition as claimed inclaim 5, comprising a further herbicide.
 9. A method for controlling anunwanted plant, which comprises applying an effective amount of at leastone compound of formula (I) and/or salt thereof as claimed in claim 1,to a plant and/or to a site of unwanted vegetation.
 10. The compound offormula (I) and/or salt thereof as claimed in claim 1, capable of beingused for controlling an unwanted plant.
 11. The compound of formula (I)and/or salt thereof as claimed in claim 10, wherein said compound offormula (I) is used for controlling an unwanted plant in a crop of auseful plant.
 12. The compound of formula (I) and/or salt thereof asclaimed in claim 11, wherein said useful plant is a transgenic usefulplant.
 13. A method for controlling an unwanted plant, which comprisesapplying an effective amount of a herbicidal composition as claimed inclaim 3, to a plant and/or to a site of unwanted vegetation.
 14. Theherbicidal composition as claimed in claim 3, is capable of being usedfor controlling an unwanted plant.